Water → 2-Hydroxy-2-phenylcyclopentanone

HRID 262005

Reaction equation

HRID 262005 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[C:8]1([Li])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CCOCC>[OH:6][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4][CH2:5][C:1]1=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 5666571,2-CyclopentanedioneHCID 178506676HCID 178506676, compound

Product 1

HCID 105834112-Hydroxy-2-phenylcyclopentanoneYield 58.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 73.5 g (0.75 mole) of 1,2-cyclopentanedione in 400 ml of ether was added to 1.5 moles of phenyl lithium in 1.2 liter of ether, and the mixture was stirred under N2 for one half hour. After careful addition of water, the ethereal layer was separated, dried over magnesium sulfate and the solvent evaporated. The residue was distilled under reduced pressure and gave 77.2 g of 2-hydroxy-2-phenylcyclopentanone, b.p. 122°-126° C. (1.5 mm), nD25 1.5551. The oxime was prepared by known procedures, m.p. 110°-112° C., and was reduced by hydrogenation over Raney nickel in 20% alcoholic ammonia. Removal of catalyst, evaporation of solvent and addition of HCl gave 2-hydroxy-2-phenylcyclopentylamine hydrochloride, m.p. 198°-199° C.

Workup

  1. customthe ethereal layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent evaporated
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-260956d20daf47358c399d0a535b462b
Source dataset
uspto-grants-1979_05
Patent number
US04153235

Linked notes

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