Acetaldehyde → Ethyl 2-ethylidene-4-chloro-3-oxobutyrate

HRID 1649412

Reaction equation

HRID 1649412 reaction equation
N1CCC[CH2:3][CH2:2]1.[Cl:7][CH2:8][C:9](=[O:14])[CH2:10][C:11]([OH:13])=[O:12].[CH:15](=O)[CH3:16]>C(OCC)(=O)C>[CH2:2]([O:12][C:11](=[O:13])[C:10](=[CH:15][CH3:16])[C:9](=[O:14])[CH2:8][Cl:7])[CH3:3]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 8082PiperidineHCID 119720Butanoic acid, 4-chloro-3-oxo-

Product 1

HCID 54518096Ethyl 2-ethylidene-4-chloro-3-oxobutyrate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 g of piperidine were dropped into a stirred mixture of 82 g of 4-chloroacetoacetic acid and 24 g of acetaldehyde at -20°. After stirring the mixture at -10° to -20° for 7 hours 100 ml of ethyl acetate were added and the solution was subsequently extracted three times with ice-cold 1 n hydrochloric acid and with water. The organic phase was dried over magnesium sulphate and concentrated. The oil which remained was subjected to Kugelrohr-distillation under a high vacuum.

Workup

  1. additionwere added
  2. extractionthe solution was subsequently extracted three times with ice-cold 1 n hydrochloric acid
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationThe oil which remained was subjected to Kugelrohr-distillation under a high vacuum

Sources & evidence

ORD record
ord-c1952970ff0444f1beaa4929b2a3bb5b
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Linked notes

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