Methanol → Acetic acid, 2-(2-chloroethyl)thio-, methyl ester

Reaction equation

S(Cl)(Cl)=O.[Cl:5][CH2:6][CH2:7][S:8][CH2:9][C:10]([OH:12])=[O:11].[CH3:13]O>>[CH3:13][O:11][C:10](=[O:12])[CH2:9][S:8][CH2:7][CH2:6][Cl:5]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2302472-[(2-Chloroethyl)sulfanyl]acetic acid

Product 1

HCID 51933Acetic acid, 2-(2-chloroethyl)thio-, methyl ester

Conditions

Temperature: 5 °C

Procedure

Thionyl chloride (10 ml) was added to a solution of the title compound of Example 9 (9.7 g, 0.06 mole) in methyl alcohol (100 ml) cooled to 5° C. via an ice bath. The ice bath was removed and the reaction stirred for 2.5 hours at room temperature. The methyl alcohol and excess thionyl chloride were removed using a rotary evaporator to give 9.8 g, of an oil which was identified by NMR as the title compound.