Formaldehyde → 3-Cyclohexylprop-2-yn-1-ol

To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehyde (prepared from the thermal decomposition of 50 g of paraformaldehyde for 20 minutes) was bubbled into the mixture. After cooling, the reaction was quenched with saturated ammonium chloride and extracted with ether (2×100 ml). The combined ether extracts were washed with brine, dried over magnesium sulfate and evaporated to yield the product which was distilled under high vacuum at 68°-74° C. to yield 6.4 g as a colorless liquid.

1. temperaturethe reaction mixture was refluxed for 2 hours
2. customwas bubbled into the mixture
3. temperatureAfter cooling
4. customthe reaction was quenched with saturated ammonium chloride
5. extractionextracted with ether (2×100 ml)
6. washThe combined ether extracts were washed with brine
7. dry with materialdried over magnesium sulfate
8. customevaporated
9. customto yield the product which
10. distillationwas distilled under high vacuum at 68°-74° C.
11. customto yield 6.4 g as a colorless liquid

ORD record

ord-ea2fb6c87de2423b8a84f6a9a4419031

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728698