Hydrochloric Acid → 1,1,1-Trichloro-4-methylpent-4-en-2-ol

To the optically-active catalyst of Example 1 (a) (total product) under nitrogen was added a solution of chloral (3.3 ml, 33.8 mmole) in dichloromethane (dried over calcium hydride) (30 ml). After cooling the solution to 0°-5° C., isobutene gas (2.84 g, 50 mmole) was bubbled through the mixture over about 1 min. At this stage the temperature of the mixture was not allowed to rise above 20° C. After stirring the mixture at 10°-15° C. for up to 20 h, it was poured into 10% hydrochloric acid (30 ml). After shaking the phases, the aqueous layer was separated and extracted with fresh dichloromethane (2×30 ml). The combined organic extracts were washed with water (30 ml) and dried (MgSO4). Concentration of the extract gave a red oil (6.55 g, 95%) which was distilled to give the product as a colourless oil, with physical characteristics identical to those reported in the literature.

1. temperatureAfter cooling the solution to 0°-5° C.
2. customto rise above 20° C
3. stirringAfter shaking the phases
4. customthe aqueous layer was separated
5. extractionextracted with fresh dichloromethane (2×30 ml)
6. washThe combined organic extracts were washed with water (30 ml)
7. dry with materialdried (MgSO4)

ORD record

ord-134de1387033450ea2792f3aee92ce7c

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04933511