3-Hydroxy-2,2-dimethylpropionaldehyde → HCID 10942910, 화합물

HRID 392538

반응식

HRID 392538 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 10942910HCID 10942910, 화합물수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-17eeb139b8744ab1893b91d55b360ab8
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800772B2

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