Methanol → 4-Hydroxy-1-phenylcyclohexane-1-carbonitrile

HRID 2398809Notes

Reaction equation

HRID 2398809 reaction equation
CO.[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)#[N:4].[BH4-].[Na+]>O1CCCC1>[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)#[N:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 4311764Sodium borohydride

Product 1

HCID 124536734-Hydroxy-1-phenylcyclohexane-1-carbonitrileYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice and methanol cooled solution of 4 g. (0.0205 M) of 4-cyano-4-phenylcyclohexanone (a) (prepared as in J. Chem. Soc. 1959, 1446) in 150 ml. of tetrahydrofuran, a suspension of 1 g. of sodium borohydride in 50 ml. of tetrahydrofuran is added in 5 ml. portions in in the course of about 10 minutes. The mixture is stirred for about 30 minutes and allowed to stand in the cold for about 18 hours. The bulk of the solvent is removed under vacuum and the residue treated with water. The precipitate is extracted with ether and the organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine and then evaporated to dryness. The residue is recrystallized with benzene to give 1.81 g. (43.8% yield) of 4-cyano-4-phenylcyclohexanol (b) melting at 103° to 111° C.

Workup

  1. customin in the course of about 10 minutes
  2. customcold for about 18 hours
  3. customThe bulk of the solvent is removed under vacuum
  4. additionthe residue treated with water
  5. extractionThe precipitate is extracted with ether
  6. washthe organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine
  7. customevaporated to dryness
  8. customThe residue is recrystallized with benzene
  9. customto give 1.81 g

Sources & evidence

ORD record
ord-a361d098cb1845f5867b705be58dc4a8
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

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