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

HRID 845076Notes

Reaction equation

HRID 845076 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

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 230247[(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.

Workup

  1. customThe ice bath was removed
  2. customThe methyl alcohol and excess thionyl chloride were removed
  3. customa rotary evaporator
  4. customto give 9.8 g

Sources & evidence

ORD record
ord-1b46faf5093c4315902965b85cf14e95
Source dataset
uspto-grants-1988_07
Patent number
US04755524

Reaction notes

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