Water → 2-Hydroxy-2-phenylcyclopentanone

HRID 262005

反応式

HRID 262005 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 5666571,2-CyclopentanedioneHCID 178506676HCID 178506676、化合物

生成物 1

HCID 105834112-Hydroxy-2-phenylcyclopentanone収率 58.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-260956d20daf47358c399d0a535b462b
出典データセット
uspto-grants-1979_05
特許番号
US04153235

関連ノート

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