Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 2420143

反応式

HRID 2420143 の反応式
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5202412-Benzylpropane-1,3-diol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Diethyl benzylmalonate (100g.) was added dropwise to a stirred suspension of lithium aluminium hydride (12g.) in anhydrous diethyl ether (300ml.) at 0° C. under argon. The reaction mixture was then stirred overnight at room temperature and worked up by the conventional procedure, described in J. Org. Chem. 1953, 18, 1190. Evaporation of the ether solution gave 2-benzylpropane-1,3-diol. Phosphorus tribromide (26ml.) was added dropwise to this diol (44g.), whilst stirring at 75° C. After the vigorous reaction had ceased, the temperature was raised to 100° C. and maintained at this temperature overnight. The cooled mixture was poured into ice water (500ml.) and extracted with diethyl ether (2 × 500ml.). The combined ether extracts were washed with aqueous sodium bicarbonate, then brine, dried over sodium sulphate and the ether was evaporated. Distillation of the crude product in vacuo gave 2-benzyl-1,3-dibromopropane b.p. 116°-121° C./1.0 mm. Hg.

後処理

  1. customEvaporation of the ether solution

出典と根拠

ORDレコード
ord-00d8f7f9095846cdb2bcfdf35853a30e
出典データセット
uspto-grants-1978_08
特許番号
US04109015

関連ノート

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