Cyclohexanone → 1-Phenylcyclohexanol

HRID 248782Notes

Reaction equation

HRID 248782 reaction equation
[Ca].F[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[C:3]1([C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 10008FluorobenzeneHCID 5460341Calcium

Product 1

HCID 153191-PhenylcyclohexanolYield 85%

Procedure

Reactions of aryl halides with reactive calcium required slightly higher temperatures, up to -30° C. for aryl bromides and up to -20° C. for aryl chlorides. The aryl calcium compounds are very stable at room temperature. Reactions of m-bromotoluene, m-bromoanisole, and p-chlorotoluene with the soluble highly reactive calcium complex gave the corresponding arylcalcium reagents in quantitative yields based on the GC analyses of reaction quenches. The 1,2-addition of these arylcalcium compounds with ketones gave the alcohols in excellent yields (76%, 79% and 86%, respectively). The soluble highly reactive calcium readily reacted with fluorobenzene at room temperature to form the corresponding organometalic compound which underwent an addition reaction with cyclohexanone to give 1-phenylcyclohexanol in 85% yield.

Workup

  1. customin excellent yields (76%, 79% and 86%
  2. customto form the corresponding organometalic compound which

Sources & evidence

ORD record
ord-05c2bf86f9974701b551dd5a6dcc815b
Source dataset
uspto-grants-1993_05
Patent number
US05211889

Reaction notes

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