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

HRID 2309681

反応式

HRID 2309681 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.[Al].[Li].[H-].[H-].[H-].[H-].[Li+].[Al+3]>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

5

反応物 3

HCID 69090Diethyl 2-benzylpropanedioateHCID 16211445Aluminum;lithiumHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5202412-Benzylpropane-1,3-diol収率 65.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of diethyl benzylmalonate (107 g, 0.43 mol) in 300 ml dry diethyl ether was added under nitrogen to a suspension of 24.5 g (0.65 mol) lithium aluminium hudride (LiAlH4) in 220 ml dry ether so to maintain a gentle reflux. The reaction mixture was refluxed for 2 more hours after the addition was completed. The excess of LiAlH4 was destroyed by addition of 50 ml ethyl acetate, followed by 50 ml water and finally by 600 ml 15% sulfuric acid. The ether phase was extracted by a saturated sodium bicarbonate solution and a saturated sodium chloride solution and dried over magnesium sulfate. Evaporation of the solvent left a white solid that was purified by recrystallization in ether. An amount of 45.8 g (0.28 mol) of 2-benzyl-1,3-propanediol was obtained (yield=64%).

後処理

  1. temperatureto maintain a gentle reflux
  2. temperatureThe reaction mixture was refluxed for 2 more hours
  3. additionafter the addition
  4. customThe excess of LiAlH4 was destroyed by addition of 50 ml ethyl acetate
  5. extractionThe ether phase was extracted by a saturated sodium bicarbonate solution
  6. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  7. customEvaporation of the solvent
  8. waitleft a white solid
  9. customthat was purified by recrystallization in ether

出典と根拠

ORDレコード
ord-d52789de329743cb8852a6a731775ce2
出典データセット
uspto-grants-1987_09
特許番号
US04696920

関連ノート

読み込み中…