Acetic Acid → 1-(5-Cyclohexyl-2-hydroxyphenyl)ethan-1-one
Reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(F)(F)F.[C:18](O)(=[O:20])[CH3:19]>>[OH:13][C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:12][C:11]=1[C:18](=[O:20])[CH3:19]Participants
Procedure
35.25 g of 4-cyclohexyl-phenol were added in small amounts at 5° to 10° C. to a solution of 46 g of boron trifluoride in 110 ml of concentrated acetic acid and the mixture was held at 50° C. for 15 minutes and then at 75° C. for 21 hours. The mixture was poured into ice and the aqueous phase was extracted 3 times with 200 ml of ether. The ether phase was treated with powdered sodium bicarbonate and was stirred for 16 hours and was then filtered. The filtrate was washed with water until the wash water was neutral, dried over magnesium sulfate and was evaporated to dryness under reduced pressure. The residue was pressure chromatographed over silica gel and was eluted with a 1-4 ether-petroleum ether (b.p.=60° to 80° C.) mixture to obtain 39.9 g of 1-(2-hydroxy-5-cyclohexylphenyl)-ethanone melting at <50° C.
Workup
- waitat 75° C. for 21 hours
- additionThe mixture was poured into ice
- extractionthe aqueous phase was extracted 3 times with 200 ml of ether
- additionThe ether phase was treated with powdered sodium bicarbonate
- filtrationwas then filtered
- washThe filtrate was washed with water until the wash water
- dry with materialdried over magnesium sulfate
- customwas evaporated to dryness under reduced pressure
- customchromatographed over silica gel
- washwas eluted with a 1-4 ether-petroleum ether (b.p.=60° to 80° C.) mixture
Sources & evidence
- ORD record
- ord-598e41d1216449668bb9d11a4c4b0f6c
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04281012
Reaction notes
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