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

HRID 392538Notes

Reaction equation

HRID 392538 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 10942910HCID 10942910, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-17eeb139b8744ab1893b91d55b360ab8
Source dataset
uspto-grants-2004_10
Patent number
US06800772B2

Reaction notes

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