2-(Ethylthio)ethanol → 2-(Ethylthio)ethyl 2-chloroethanesulfinate

HRID 2163429Notes

Reaction equation

HRID 2163429 reaction equation
[OH:1][CH2:2][CH2:3][S:4][CH2:5][CH3:6].[Cl:7][CH2:8][CH2:9][S:10](Cl)=[O:11]>CCOCC>[Cl:7][CH2:8][CH2:9][S:10]([O:1][CH2:2][CH2:3][S:4][CH2:5][CH3:6])=[O:11]

Participants

4

Reactant 2

HCID 80752-(Ethylthio)ethanolHCID 125500522-Chloroethanesulfinic chloride

Product 1

HCID 227516332-(Ethylthio)ethyl 2-chloroethanesulfinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 2-hydroxyethyl sulfide (10.6 w) in dry ether (50 v) was slowly added to 2-chloroethanesulfinyl chloride (14.7 w) in dry ether (200 v) maintained at about -10° under a nitrogen atmosphere. Upon warming to ambient temperature, the reaction mixture was evaporated under reduced pressure. The residual oil was passed through a wiped film molecular still to yield 2-(ethylthio)ethyl 2-chloroethanesulfinate (15.4 w) boiling at 95-100° under reduced pressure (1 × 10-4 torr).

Workup

  1. temperaturemaintained at about -10° under a nitrogen atmosphere
  2. customthe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-52b74871f0cc4aef9636860c257edd9a
Source dataset
uspto-grants-1979_01
Patent number
US04134752

Reaction notes

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