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3,5-Dimethoxybenzaldehyde → 1-(3,5-Dimethoxyphenyl)-7-hydroxy-1-hepten-3-one

HRID 67887
ノート
印刷プレビュー

反応式

HRID 67887 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1)[CH:33]=O>C1C=CC=CC=1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 817473,5-DimethoxybenzaldehydeHCID 11349379(5-Hydroxypentanoylmethylene)-triphenylphosphorane

生成物 1

HCID 543179781-(3,5-Dimethoxyphenyl)-7-hydroxy-1-hepten-3-one

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

10 parts of the phosphonium salt produced in Example 16 was dissolved in water containing an amount of potassium carbonate in excess of that necessary to deprotonate the phosphonium chloride. After extracting this solution with methylene chloride, the organic phase was dried over sodium sulfate. After separation of the drying agent, the methylene chloride was removed at room temperature and under a stream of nitrogen, leaving (5-hydroxypentanoylmethylene)-triphenylphosphorane. 7.04 parts of this phosphorane and 3.11 parts of 3,5-dimethoxybenzaldehyde were dissolved in about 135 parts of benzene, and the solution was maintained under a nitrogen atmosphere and refluxed for 3 days. After the reaction mixture was cooled to room temperature, the benzene was removed at room temperature under a nitrogen stream, leaving a product mixture. This mixture was separated chromatographically on a silica column using as the elution solvent a mixture of 30 percent by volume of ethyl acetate in benzene, to yield 1-(3,5-dimethoxyphenyl)-7-hydroxy-1-hepten-3-one which, after recrystallization from a mixture of benzene and cyclohexane, melted at about 78°-80° C.

後処理

  1. temperaturethe solution was maintained under a nitrogen atmosphere
  2. temperaturerefluxed for 3 days
  3. customthe benzene was removed at room temperature under a nitrogen stream
  4. customleaving a product mixture
  5. customThis mixture was separated chromatographically on a silica column
  6. additiona mixture of 30 percent by volume of ethyl acetate in benzene

出典と根拠

ORDレコード
ord-0d9aa5349b4f4cf396fd0ad3779782ab
出典データセット
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04347192

反応ノート

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