Sodium borohydride → 4-(p-Fluorophenyl)-3-cyclohexen-1-ol

HRID 1657559Notes

Reaction equation

HRID 1657559 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22610268HCID 22610268, compound

Product 1

HCID 215344654-(p-Fluorophenyl)-3-cyclohexen-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.065 mole of 4-(p-fluorophenyl)-3-cyclohexen-1-one (obtained as in Example 7) and 6 g. of sodium borohydride in 130 ml. of ethanol is stirred at room temperature for about 5 hours. The bulk of the solvent is removed on a rotary evaporator and the residue diluted with water. The precipitated solid is collected on a filter and recrystallized from Skellysolve B to give a 96% yield of 4-(p-fluorophenyl)-3-cyclohexen-1-ol having a melting point of 73° to 74.5° C.

Workup

  1. customThe bulk of the solvent is removed on a rotary evaporator
  2. additionthe residue diluted with water
  3. customThe precipitated solid is collected on
  4. filtrationa filter
  5. customrecrystallized from Skellysolve B

Sources & evidence

ORD record
ord-9c2bafb466cb476e89c4de00865d83b5
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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