反应详情

To a cold solution of sodium hydroxide (9.75 g, 240 mmol) in methanol (200 mL) was added thioglycollic acid (11.25 g, 120 mmol) slowly over 30 min. Sodium thioglycollate precipitated and was redissolved by stirring and warming the mixture. The sodium thioglycollate solution was then cooled to room temperature and 4-methoxy-3-nitrobenzyl chloride (30.0 g, 120 mmol) was added in portions to reduce the intensity of exothermic reaction. The resulting mixture was heated to reflux temperature and maintained at reflux temperature for 4 h. The heated mixture was then cooled and poured onto crushed ice (1 kg) containing hydrochloric acid (50 mL). A precipitate formed. The precipitate was separated by filtration, washed with ice cold water and dried under vacuum to yield 30 g (95% yield) of the desired 4-methoxy-3-nitrobenzylthioacetic acid product. m.p. 130-132° C.

1. customSodium thioglycollate precipitated
2. dissolutionwas redissolved
3. temperaturewarming the mixture
4. customthe intensity of exothermic reaction
5. temperatureThe resulting mixture was heated
6. temperatureto reflux temperature
7. temperaturemaintained
8. temperatureat reflux temperature for 4 h
9. temperatureThe heated mixture was then cooled
10. additionpoured
11. customA precipitate formed
12. customThe precipitate was separated by filtration
13. washwashed with ice cold water
14. customdried under vacuum