Chloral → 1,1,1-Trichloro-4-methylpent-4-en-2-ol

Temperature

0 °C

A mixture of anhydrous chloral (738 g), isobutylene (309 g), and petroleum ether (boiling range 40° to 60° C, 800 ml) was stirred at a temperature in the range -5° to -8° C whilst aluminium chloride (54.5 g) was added in small portions over a period of 2 hours. The mixture was stirred for a further period of one hour at 0° C. Water (450 ml) was then added over 15 minutes, the temperature being maintained at 0° C, after which the mixture was allowed to attain to the ambient temperature. The organic phase was separated, washed with brine (3 × 250 ml) and dried over anhydrous magnesium sulphate. After removal of the solvent by evaporation under reduced pressure the residual oil was distilled under reduced pressure and the fraction boiling range 101° to 111° C at 16 to 18 mm Hg pressure collected. This was shown by gas liquid chromatographic examination to consist of approximately 90%, 1,1,1-trichloro-2-hydroxy-4-methyl-4-pentene and approximately 10% 1,1,1-trichloro-2-hydroxy-4-methyl-3-pentene. Careful distillation afforded almost pure (by g.l.c.) 1,1,1-trichloro-2-hydroxy-4-methyl-4-pentene as a colourless oil (boiling point 99° -100° C/16 mm Hg).

1. additionwas added in small portions over a period of 2 hours
2. temperaturethe temperature being maintained at 0° C
3. customto attain to the ambient temperature
4. customThe organic phase was separated
5. washwashed with brine (3 × 250 ml)
6. dry with materialdried over anhydrous magnesium sulphate
7. customAfter removal of the solvent
8. customby evaporation under reduced pressure the residual oil
9. distillationwas distilled under reduced pressure
10. customthe fraction boiling range 101° to 111° C at 16 to 18 mm Hg pressure collected
11. distillationCareful distillation

ORD record

ord-84c4d36a1a5e47178d5f2367195c63e2

Source dataset

uspto-grants-1977_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04018838