Extracurricular laboratory: Synthetic route of P-anisaldehyde dimethyl acetal

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Adding a certain compound to certain chemical reactions, such as: 2186-92-7, name is P-anisaldehyde dimethyl acetal, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2186-92-7, HPLC of Formula: C10H14O3

7-Anisaldehyde dimethylacetal (50 mL, 294 mmol, 1.14 equiv) was added to a suspension of a mixture of methyl a-D-glucopyranoside (50 g, 257 mmol) and D- camphorsulfonic acid (1.79 g, 7.72 mmol, 0.03 equiv) in DMF (250 mL). The reaction mixture was stirred at 60 C for 21 h. After cooling to rt, the solution was concentrated under reduced pressure. A saturated sodium bicarbonate aqueous solution (500 mL) was added to the residue and the resulting mixture was stirred for 1 h. The precipitate was filtered and washed with cold aqueous saturated sodium bicarbonate solution (500 mL) to provide methyl 4,6-O-(4-methoxy)benzylidene-a-D-galactopyranoside (78.5 g, 98%) as a colorless solid, mp: 192-194 C; 1H NMR (CD3OD, 600 MHz) delta = 7.40 (d, 2H, J = 8.4 Hz, CH of Ar), 6.88 (d, 2H, J = 8.4 Hz, CH of Ar), 5.51 (s, IH, ArCH), 4.71 (d, IH, J = 3.8 Hz, H- l), 4.18 (dd, IH, J = 8.1 Hz, 3.3 Hz, H-6?), 3.81-3.78 (m, IH, H-4), 3.78 (s, 3H, OCH3 of An), 3.74-3.68 (m, 2H, H-3, H-6P), 3.50 (dd, IH, J = 9.3 Hz, 3.8 Hz, H-2), 3.43-3.40 (m, IH, H-5), 3.42 (s, 3H, OCH3); 13C NMR (CD3OD, 125 MHz) delta = 161.6, 131.5, 128.8, 114.3, 103.0, 102.0, 82.9, 74.1, 72.0, 70.0, 63.9, 55.8, 55.7; HRMS (ESI) Calcd for Ci5H2107 [M+H]+: 313.1287

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