反应详情

Anisoin (2.87 g), 100 mL of methylene chloride, and pyridine (2.02 g) are placed in a flask under nitrogen. Thionyl chloride (1.60 ml) is added dropwise over 5 minutes using a water bath to maintain the reaction temperature between 25° C. and 30° C. After allowing the mixture stir for 50 minutes the reaction is quenched by washing with water (2×100 mL) and 100 mL of brine. The organics are dried over sodium sulfate, filtered, then concentrated. The resulting oil is taken up in 25 mL of diethyl ether and filtered. The filter cake is rinsed with 25 ml of diethyl ether. To the filtrate is added 25 ml of ethanol and the solution is concentrated. Crystals are allowed to form over 24 hours. The precipitate which forms is filtered, washed with 25 mL of ethanol, and dried in vacuo at 45° C. to give 4.00 g of product. (69%). Analysis calculated for C16H14ClO3 : C, 66.10; H, 5.20; Cl, 12.19. Found: C, 66.29; H, 5.32; Cl, 12.56. MS(FD) 290.

1. temperatureto maintain the reaction temperature between 25° C. and 30° C
2. customis quenched
3. washby washing with water (2×100 mL) and 100 mL of brine
4. dry with materialThe organics are dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. filtrationfiltered
8. washThe filter cake is rinsed with 25 ml of diethyl ether
9. additionTo the filtrate is added 25 ml of ethanol
10. concentrationthe solution is concentrated
11. customto form over 24 hours
12. filtrationThe precipitate which forms is filtered
13. washwashed with 25 mL of ethanol
14. customdried in vacuo at 45° C.