Water → 2-Hydroxy-2-phenylcyclopentanone

HRID 262005

반응식

HRID 262005 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 105834112-Hydroxy-2-phenylcyclopentanone수율 58.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-260956d20daf47358c399d0a535b462b
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153235

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