Category: 10103-06-7

Synthetic Route of 10103-06-7, A common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(a) 1-(6,7-Dimethoxy-naphthalen-2-yl)-2-methyl-propan-1-one The solution of 2,3-dimethoxynaphthalene (16.5 g), isobutyroylchloride (12.5 g) and aluminum chloride (15.7 g) in methylene chloride (200 ml) was stirred at ambient temperature overnight. The solution was then washed with saturated sodium bicarbonate and water, dried with sodium sulfate and evaporated. Finally the crude product was triturated with ether. Yield: 13.5 g, melting point 103-105 C. 1H-NMR (DMSO-d6): 8.51 (s,1H), 7.83 (s,2H), 7.53 (s,1H), 7.39 (s,1H), (s,3H), 3.91 (s,3H), 3.76-3.80 (m,1H), 1.16 (d,6H, J=8 Hz).

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 10103-06-7 as follows. Application In Synthesis of 2,3-Dimethoxynaphthalene

EXAMPLE 9 2-(4-Chlorobutyl)-6,7-dimethoxynaphthalene Aluminum chloride (25.5 g, 0.19 mole) was added to a solution of 21.5 mL (0.19 mole) of 4-chlorobutyryl chloride in 225 mL of methylene chloride. To the resulting solution, cooled in an ice bath, was added dropwise a solution of 30.0 g (0.16 mole) of 2,3-dimethoxynaphthalene in 150 mL of methylene chloride over 30 minutes. The reaction mixture was stirred at 3 C. for 30 minutes and at 24 C. for 17 hours. The reaction mixture was worked up as Example 5 and the crude product was recrystallized from acetone-hexane, to give 31.5 g (68% yield), mp 98-99, of 4-chloro-1-(6,7-dimethoxy-2-naphthalenyl)-1-butanone. Anal Calcd. for C16 H17 ClO3: C, 65.64; H, 5.85; Cl, 12.11. Found: C, 65.33; H, 5.77; Cl, 12.16.

According to the analysis of related databases, 10103-06-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4937371; (1990); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 10103-06-7, A common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(a) 1-(6,7-Dimethoxy-naphthalen-2-yl)-2-methyl-propan-1-one The solution of 2,3-dimethoxynaphthalene (16.5 g), isobutyroylchloride (12.5 g) and aluminum chloride (15.7 g) in methylene chloride (200 ml) was stirred at ambient temperature overnight. The solution was then washed with saturated sodium bicarbonate and water, dried with sodium sulfate and evaporated. Finally the crude product was triturated with ether. Yield: 13.5 g, melting point 103-105 C. 1H-NMR (DMSO-d6): 8.51 (s,1H), 7.83 (s,2H), 7.53 (s,1H), 7.39 (s,1H), (s,3H), 3.91 (s,3H), 3.76-3.80 (m,1H), 1.16 (d,6H, J=8 Hz).

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10103-06-7, name is 2,3-Dimethoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2,3-Dimethoxynaphthalene

General procedure: To [Ir(COD)OMe]2 (7.3 mg, 11 mumol) and 4,4′-di-tert-butyl-2,2′-bipyridine (7.0 mg, 26 mumol) in a flame-dried vial under nitrogen were added THF (0.7 mL), pinacolborane (0.18 mL, 1.24 mmol) and 1,4-dimethoxynaphthalene (7) (188 mg, 1.0 mmol). The mixture was stirred at 80 C for 24 h then filtered through Celite and concentrated in vacuo to afford crude pinacol ester 13 (100% conversion by 1H NMR) that was used directly in the next step.

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hume, Paul; Furkert, Daniel P.; Brimble, Margaret A.; Tetrahedron Letters; vol. 53; 29; (2012); p. 3771 – 3773;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10103-06-7, name is 2,3-Dimethoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

A mixture of 2,3-dimethoxynaphthalene (1.1 g, 5.85 mmol) was dissolved in 17 mL of dry 1,2-dichloroethane, Acetyl chloride (0.5 mL, 7.0 mmol) was added and AlCl3 (2.1 g, 15.75 mmol) was added in portions at 0 C for 12 hours. 15 g of ice and 5 mL of concentrated hydrochloric acid were added, the organic phase was separated and the aqueous phase was extracted with dichloromethane The organic phase was dried over anhydrous sodium sulfate, concentrated by filtration and separated by flash chromatography on CH2Cl2 to give 6,7-dimethoxy-2-naphthoethanone in 83.6% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10103-06-7.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10103-06-7, name is 2,3-Dimethoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 10103-06-7

EXAMPLE 1; 2-(l-(6,7-bis(difluoro methoxy)naphthalen-2-yl)-2-methylpropyl)-2H-tetrazole (1)To a stirred solution of A (40 g, 0.21 mol) in CH2CI2 (600 mL) was added isobutyryl chloride (34 mL, 0.31 mol) at -5 C, followed by portion- wise addition of AICI3 (56.8 g, 0.42 mol) over a period of 20 min under N2 atmosphere. The reaction was allowed to slowly warm to RT and stirred for 3h; the reaction mixture was poured into ice-cold water (200 mL) and the organic layer was separated. The aqueous layer was then extracted with CH2CI2 (2 x 100 mL); combined organic extracts were washed with 5% NaHC03 solution (100 mL), water (100 mL), brine (100 mL) and dried over anhydrous Na2S04. After filtration and evaporation under reduced pressure, the crude material was washed with w-hexane to afford B (35 g, 0.13 mol, 63%) as off-white solid. 1H NMR (200 MHz, CDC13): delta 8.34 (s, 1 H), 7.90 (dd, / = 8.6,1.8 Hz, 1 H), 7.73 (d, / = 8.6 Hz, 1 H), 7.26 (s, 1 H), 7.14 (s, 1 H), 4.03 (s, 6 H), 3.79-3.63 (m, 1 H), 1.27 (d, / = 7.0 Hz, 6H). MS (ESI): mlz 259 [M+H]+.To a stirred solution of B (18 g, 69 mmol) in CH2C12 (180 mL) was added BBr3 (87.2 g, 348 mmol) drop wise at -40 C. After completion of addition, stirring was continued for addition 1 h at -40 C and 1 h at RT. The reaction mixture was poured into cold water and aqueous layer was then extracted with CH2CI2 (2 x 200 mL). Combined organic extracts were washed with water (100 mL), brine (100 mL) and dried over anhydrous Na2S04. After filtration and evaporation of solvent under reduced pressure, the crude material was purified by column chromatography (Si02, 100-200 mesh) to afford C (9.0 g, 39 mmol, 56%) as brown color solid. 1H NMR (200 MHz, CDC13): delta 8.29 (s, 1 H), 7.88 (dd, / = 8.8, 1.6 Hz, 1 H), 7.68 (d, / = 8.6 Hz, 1 H), 7.36 (s, 1 H), 7.26 (s, 1 H), 5.88 (br s, 2 H), 3.79-3.63 (m, 1 H), 1.27 (d, / = 6.8 Hz, 6 H).To a stirred solution of C (10.0 g, 0.043 mol) in DMF (100 mL) were added sodium 2-bromo-2,2- difluoroacetate (42.6 g, 0.21 mol) (the Na salt was prepared by treating ester with 1.0 eq of NaOH in EtOH: H20 (2:1) at RT for 16. Then solvent was evaporated and residue was co-distilled with toluene (3 times) to obtain the salt.) and K2C03 (36 g, 0.26 mol) and the mixture was stirred at 80- 90 C for 48 h. The reaction mixture was poured into cold water and aqueous layer was then extracted with CH2C12 (3 x 100 mL). Combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over anhydrous Na2S04. After filtration and evaporation of solvent under reduced pressure, the crude material was purified by column chromatography (Si02, 100- 200 mesh) to afford D (3.0 g, 0.009 mol, 21%) as a solid. 1H NMR (500 MHz, CDC13): delta 8.40 (s, 1 H), 8.05 (dd, / = 8.5, 1.5 Hz, 1 H), 7.86 (d, / = 9.0 Hz, 1 H), 7.79 (s, 1 H), 7.68 (s, 1 H), 6.67 (t, JF.H = 73 Hz, 1 H), 6.65 (t, JF>H = 73 Hz, 1 H), 3.72-3.65 (m, 1 H), 1.27 (d, / = 7.0 Hz, 6 H). To a stirred solution of D (0.65 g, 1.96 mmol) in MeOH (10 mL) was added NaBH4 (0.15 g, 3.9 mmol) at 0 C and the resulting mixture was stirred for additional 30 min at 0 C. The reaction mixture was quenched with ice-cold water and the aqueous layer was then extracted with EtOAc (2 x 50 mL). Combined organic extracts were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude material was purified by column chromatography (Si02, 100-200 mesh) using gradients of EtOAc/hexane to afford E (0.58 g, 1.74 mmol, 89%) as a semi solid. 1H NMR (200 MHz, CDC13): delta 7.80-7.72 (m, 2 H), 7.64 (s, 2 H), 7.50 (dd, / = 8.4, 1.8 Hz, 1 H), 6.63 (t, JF>H = 72 Hz, 2 H), 4.58-4.53 (m, 1 H), 2.10-2.00 (m, 1 H), 1.95 (d, / = 3.0 Hz, 1 H), 1.00 (d, / = 6.8 Hz, 3 H), 0.84 (d, / = 6.8 Hz, 3 H).To a stirred solution of E (0.8 g, 2.4 mmol) in acetonitrile (15 mL) was added thionyl chloride (0.27 mL, 3.61 mmol) at 0 C and the resulting reaction mixture was stirred for additional 30 min at 0 C. The reaction mixture was quenched with water (20 mL) and the aqueous layer was then extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with 5% NaHC03 solution (50 mL), water (50 mL), brine (50 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure to afford F (0.8 g, 2.28 mol, 95%) as solid. 1H NMR (200 MHz, CDCI3): delta 7.81-7.72 (m, 2 H), 7.65 (s, 2 H), 7.53 (dd, / = 8.6,1.8 Hz, 1 H), 6.62 (t, JF>H = 74 Hz, 2 H), 4.75 (d, / = 8.0 Hz, 1 H), 2.38-2.28 (m, 1 H), 1.14 (d, / = 6.4 Hz, 3 H), 0.87 (d, / = 6.8 Hz, 3 H).To a stirred solution of F (0.3 g, 0.85 mmol) in DMF (5 mL) were added K2C03 (0.47 g, 3.41 mmol) and IH-tetrazole (0.18 g, 2.56 mmol) at RT. The reaction mixture was heated at 90 C for 36 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL); combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over anhydrous Na2S04. After filtration and evaporation of solvent under reduced pressure, the crude mater…

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, William, J.; SCHOTZINGER, Robert, J.; RAFFERTY, Stephen, William; WO2011/82245; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 10103-06-7,Some common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A suspension of aluminium chloride (6.02g, 0.0451 mol) in sieve-dried nitrobenzene (10 mL) was cooled in an ice-bath and acetyl chloride (3.57 mL, 3.93 g, 0.0501 mol) added over 5 minutes. 2,3-Dimethoxynaphthalene (7.52 g, 0.0400 mol) in nitrobenzene (25 mL) was then added over 10 minutes. The reaction was stirred for a further 60 minutes at [0C] and then left overnight at room temperature. The mixture was poured onto a mixture of ice (60 g) and 10% [HC1] (100 mL). Chloroform (300 mL) was added and the two phases separated. The aqueous was further extracted with chloroform (2 x 150 mL) and the combined organics then washed with 5% aqueous sodium hydroxide (3 x 100 mL) and water (2 x 100 mL), dried (anhydrous Na2SO4), filtered and evaporated under vacuo to give a brown oil. This was flash column chromatographed (silica gel, chloroform) to give 6,7-dimethoxy-2-acetonaphthone (8.51 g. 93% yield) as an orange solid. A sample was further recrystallised from ethanol to give fine orange needles; Rf:0. 36 (CHCl3), 0.62 (25: 1 [CHCL3] : MeOH), mp: [100-102C,] lit. mp: [113-116C] ; ‘H NMR [(CDC13/TMS)] : [8] 2.69 (s, 3H, [COCH3),] 4.02 (s, 3H, [OCH3),] 4.03 (s, 3H, OCH3), 7.14 (s, [1H,] H-8), 7.22 (s, [1H,] H-5), 7.72 (d, [1H,] [J4,] 3 8.4 Hz, H-4), 7.89 (dd, [1H,] [3, 1] 1.7 Hz, H-3), 8.33 (bs, [1H,] H-1) ; LRESI mass spectrum : [NZLZ] 231 (100%, MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; CORTICAL PTY LTD; WO2003/104178; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 10103-06-7,Some common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(a) 2,3-Dimethoxy-naphthalene-1-carbaldehyde n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N’,N’-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0 C. The reaction mixture was stirred at room temperature for two hours, cooled to 0 C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g. 1H-NMR (DMSO-d6, 400 MHz): 10.68 (s,1H, CHO), 8.95-8.97 (m, 1H), 7.87-7.89 (m,1H), 7.80 (s,1H), 7.49-7.51 (m,2H), 4.00 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 10103-06-7, A common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(a) 1-(6,7-Dimethoxy-naphthalen-2-yl)-heptan-1-one Aluminium chloride (2.66 g) was added to a solution of: heptanoylchloride (3.1 ml) and 2,3-dimethoxynaphthalene (3.76 g) in methylene chloride (50 ml) at 0 C. The reaction mixture was stirred at room temperature overnight and then worked up as described in example 3(a). The crude product was recrystallized from ethanol. Yield: 2.8 g, melting point 77-78 C. 1H-NMR (DMSO-d6, 400 MHz): 8.49 (s,1H), 7.81 (s,2H), 7.51 (1H); 7.18 (s,1H), 3.92 (s,3H), 3.91 (s,3H), 3.07 (t,2H, J=8 Hz), 1.61-1.68 (m,2H), 1.29-1.37 (m,8H), 0.87 (t,3H, J=8 Hz).

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem