Reaction #1328420

Reaction equation

methyl 2-chlorosulfonyl-4-chlorobenzoate

→

Methyl 2-mercapto-4-chlorobenzoate

Solvents

hydrochloric acid

—

ice

Conditions

Workup

1. 1
   workup.WAITAfter 2 hours at this temperature
2. 2
   Temperaturethe mixture was cooled
3. 3
   workup.WAITto stand at room temperature for 12 hours
4. 4
   Extractionextracted with ethyl acetate
5. 5
   Otherthe combined organic phases were dried
6. 6
   Otherthe solvent was removed

Procedure

Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were added a little at a time to a suspension of 205 g (0.75 mol) of methyl 2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloric acid and 375 g of ice. The mixture was stirred for another 3 hours and slowly heated to 70° C. After 2 hours at this temperature, the mixture was cooled. The reaction mixture was allowed to stand at room temperature for 12 hours and then extracted with ethyl acetate, the combined organic phases were dried and the solvent was removed. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

Source