Sodium Hydroxide → (2-phenylcyclopropyl)methanol

HRID 2051391Notes

Reaction equation

HRID 2051391 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[B].[OH-].[Na+]>C1COCC1>[OH:11][CH2:10][C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 5462311Boron

Product 1

HCID 1561175(2-phenylcyclopropyl)methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1st stage: add a solution of 25.0 g (154 mmol) of trans-2-phenylcyclopropanecarboxylic acid in 100 ml of THF to a boron complex borane-THF solution drop by drop under a nitrogen atmosphere. Place the solution in the reflux for 3 hours and gently add 130 ml of NaOH 2N solution and stir the mixture for 30 minutes. Concentrate the etherised extracts in a vacuum to obtain 20.78 g of coarse trans-1-hydroxymethyl-2-phenylcyclopropane which is purified by distillation.

Workup

  1. temperaturereflux for 3 hours
  2. concentrationConcentrate the etherised extracts in a vacuum

Sources & evidence

ORD record
ord-d5b9715621bc4412a8ef8c7212e4214d
Source dataset
uspto-grants-1991_05
Patent number
US05017723

Reaction notes

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