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;,
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