Hydrochloric Acid → HCID 12898548, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylaniline (20.0 g=70 mmol), add 50 ml 4 N HCl. Reflux 1 hr., cool to 0° C., and add over 1 hour NaNO2 (6.0 g=87 mmol) in 13 ml H2O. After 30 min., add to a 45° C. solution of potassium ethylxanthate (14.3 g=83 mmol) in 40 ml H2O. Keep at 45° C. for 30 minutes, cool, and extract with ether. Dry and concentrate. Dissolve the oil in 100 ml EtOH, add potassium hydroxide (17.5 g) and reflux 1 hour. Concentrate, then add 50 ml water and 10 ml concentrated sulfuric acid. Add 0.5 g zinc dust and steam distill. Extract the distillate with ether, dry and concentrate. Recrystallize from hexane to obtain 4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylthiophenol, m.p. 62°-64° C.

Provenance & Evidence