Glycol monoethyl ether → 2-(Chloroethanesulfinyloxy)ethyl 2-chloroethanesulfinate

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).

1. additionDuring the addition period the temperature of the reaction
2. customwas controlled at -20° by external cooling
3. additionUpon completion of the addition
4. customthe solvent was removed by distillation in a vacuum
5. dissolutionThe residue was then redissolved in dry ether (200 v)
6. additionfurther treated with 2-chloroethanesulfinyl chloride (14.7 w) as above
7. customwas obtained which
8. customafter purification in a wiped film molecular still

ORD record

ord-1ea2fb48474240e0aa750c38425de706

Source dataset

uspto-grants-1979_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04134752