3-Hydroxy-2,2-dimethylpropionaldehyde → HCID 10942910、化合物

HRID 392538

反応式

HRID 392538 の反応式
[CH3:1][C:2]([CH3:7])([CH2:5]O)[CH:3]=[O:4].[C:8]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:10][CH2:11][CH3:12])=[O:9]>ClCCl>[CH3:7][C:2]([CH3:1])([CH2:3][OH:4])/[CH:5]=[CH:13]/[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

4

反応物 2

HCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

生成物 1

HCID 10942910HCID 10942910、化合物収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2,2-dimethyl-3-hydroxypropanal (22 g, 0.22 mol) and (carboethoxymethylene)triphenylphosphorane (75 g, 0.22 mol) in dry dichloromethane (150 ml) was refluxed for 46 h. The solvent was then evaporated and the crude product was distilled at 15 Torr through a very short column. The distillate was separated into two fractions by redistillation through a 40-cm Widmer column. The first fraction gave 22.3 g (60%) of ethyl trans-4,4-dimethyl-5-hydroxypent-2-enoate, b.p. 133 136° C./15 Torr, nD23 1.4641. 1H NMR (CDCl3): (=1.10 [s, 6H, C(CH3)2], 1.25 (t, 3H, CH3CH2), 3.40 (s, 2H, CH2), 3.80 (br. s, 1H, OH), 4.15 (q, 2H, CH2CH3), 5.80 (d, 1H, J=16 Hz, 3-H), 6.94 (d, 1H, J=16 Hz, 2-H). Anal. Calcd. for C9H16O3: C, 62.76; H, 9.36. Found: C, 62.92; H, 9.50.

後処理

  1. customThe solvent was then evaporated
  2. distillationthe crude product was distilled at 15 Torr through a very short column
  3. customThe distillate was separated into two fractions by redistillation through a 40-cm Widmer column

出典と根拠

ORDレコード
ord-17eeb139b8744ab1893b91d55b360ab8
出典データセット
uspto-grants-2004_10
特許番号
US06800772B2

関連ノート

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