2-Bromoethanol → 2-Bromoethyl 3-oxobutanoate

HRID 982003Notes

Reaction equation

HRID 982003 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[CH2:5]=[C:6]1[O:10][C:8](=[O:9])[CH2:7]1>ClCCl.CN(C)C1C=CN=CC=1.CC(C)=O>[C:8]([O:4][CH2:3][CH2:2][Br:1])(=[O:9])[CH2:7][C:6]([CH3:5])=[O:10]

Participants

6

Reactant 2

HCID 108982-BromoethanolHCID 12661Diketene

Product 1

HCID 132313632-Bromoethyl 3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

250 g of 2-bromoethanol are dissolved in 1.3 l of dichloromethane, and 1.2 g of 4-dimethylaminopyridine are added. 400 ml of a 50% strength diketene solution in acetone are added dropwise with vigorous stirring, so that the solvent boils moderately. After the dropwise addition, stirring is continued for a further 1 h at the boiling point and the mixture is then left to stand overnight. After the solvent has been evaporated off in a rotary evaportor in vacuo, the residue is distilled. 402 g of the title compound of b.p. 80°-83° C./0.04 mbar are obtained.

Workup

  1. additionAfter the dropwise addition
  2. waitthe mixture is then left
  3. waitto stand overnight
  4. customAfter the solvent has been evaporated off in a rotary evaportor in vacuo
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-7f5bd4a188974ec08fe9326536711114
Source dataset
uspto-grants-1991_02
Patent number
US04994461

Reaction notes

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