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温度

0 °C

4-Formylbenzoic acid (1ad, 1.00 g, 6.7 mmol) was dissolved in dry methanol (200 ml) and stirred for 10 min at 0° C. Thionyl chloride (6 ml, 82.3 mmol) was added dropwise and the mixture stirred for 90 min at 0° C. and 3 hr at room temperature. The methanol was evaporated and the resulting residue extracted into dichloromethane, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from hexane to give 1.07 g (98%) of a white solid: mp 60-62° C. [expected mp 61° C.]; 1H NMR: δ 3.87 (s, 3H), 8.01 (d, 2H, J=7.9 Hz), 8.13 (d, 2H, J=7.6 Hz), 10.08 (s, 1H); 13C NMR: δ 52.7, 129.7, 129.9, 134.4, 139.1, 165.6, 192.9.

1. stirringthe mixture stirred for 90 min at 0° C. and 3 hr at room temperature
2. customThe methanol was evaporated
3. extractionthe resulting residue extracted into dichloromethane
4. washwashed with saturated sodium chloride
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated
8. customto afford a solid
9. customThe crude solid was recrystallized from hexane