2-chloroethanesulfinyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of thallium (I) phenoxide (28.6 w) in dry ether (100 v) was rapidly treated with 2-chloroethanesulfinyl chloride, prepared as in Example I. The slurry was vigorously stirred for 1 hour at ambient temperature with exclusion of moisture. Removal of thallium(I) chloride by filtration and evaporation of the etheral filtrate solution gave an oil. The oil was then subjected to molecular distillation in a wiped-film apparatus at 70-75° (1 ×10-4 torr) to give phenyl 2-chloroethanesulfinate (122 w) as a mobile liquid. Removal of thallium(I) chloride by filtration and evaporation of the etheral filtrate solution gave an oil The oil was then subjected to molecular distillation in a wiped-film apparatus at 70-75° (1 ×10-4 torr)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). maintained at about -10° under a nitrogen atmosphere the reaction mixture was evaporated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl glycol (6.2) was added dropwise under a nitrogen atmosphere to a stirred solution of 2-chloroethanesulfinyl chloride (14.7 w), prepared as in Example I, in dry ether (40 v). During the addition period the temperature of the reaction was controlled at -20° by external cooling. Upon completion of the addition, the reaction mixture was warmed to ambient temperature and the solvent was removed by distillation in a vacuum. Examination of the residue by gas-liquid chromatography revealed more than one major component. The residue was then redissolved in dry ether (200 v) and further treated with 2-chloroethanesulfinyl chloride (14.7 w) as above. Using the same procedure as above an oily residue was obtained which after purification in a wiped film molecular still yielded a colorless liquid, 2-(chloroethanesulfinyloxy)ethyl 2-chloroethanesulfinate (8.5 w) boiling at 110-115° under reduced pressure (1 × 10-4 torr). During the addition period the temperature of the reaction was controlled at -20° by external cooling Upon completion of the addition the solvent was removed by distillation in a vacuum The residue was then redissolved in dry ether (200 v) further treated with 2-chloroethanesulfinyl chloride (14.7 w) as above was obtained which after purification in a wiped film molecular still

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Chloroethanesulfinyl chloride (16.2 w), prepared as in Example I was dissolved in dry ether (130 v) and the solution was cooled to -15°. Normal butanol was added dropwise under a nitrogen atmosphere to the cooled solution. Upon completion of the addition period the reaction mixture was allowed to warm to ambient temperatures and the solvent was removed by distillation in a vacuum to yield a colorless liquid, butyl 2-chloroethanesulfinate (18.5 w). the solution was cooled to -15° Upon completion of the addition period the reaction mixture to warm to ambient temperatures the solvent was removed by distillation in a vacuum