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Propanal → 3-Formyl-crotonic acid butyl ester

HRID 460957
Notes
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Reaction equation

HRID 460957 reaction equation
[CH2:1]([O:5][C:6](=[O:9])[CH:7]=O)[CH2:2][CH2:3][CH3:4].[CH:10](=[O:13])[CH2:11][CH3:12].C(NCCCC)CCC>CCOCC>[CH2:1]([O:5][C:6](=[O:9])/[CH:7]=[C:11](\[CH:10]=[O:13])/[CH3:12])[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 527PropanalHCID 8148DibutylamineHCID 80521Butyl oxoacetate

Product 1

HCID 867352413-Formyl-crotonic acid butyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

836 G. of the obtained glyoxalic acid butyl ester are introduced into 376 g. of propionaldehyde. The mixture is treated dropwise at 60° C. with 40.8 g of di-n-butylamine. In so doing, the reaction temperature should not rise higher than 105° C. The reaction mixture is then stirred for 2 hours at 116°-111° C., cooled and taken up in ether. The diethyl ether extract is washed successively with 500 ml. of 1 N sulphuric acid, 700 ml. of water, 1000 ml. of 5% by weight aqueous sodium bicarbonate solution and subsequently with 1000 ml. of water, dried over sodium sulphate and evaporated under reduced pressure. The remaining 3-formylcrotonic acid butyl ester boils, after rectification, at 93°-105° C./14 mm. Hg; nD25 = 1.

Workup

  1. customrise higher than 105° C
  2. temperaturecooled
  3. extractionThe diethyl ether extract
  4. washis washed successively with 500 ml
  5. dry with materialof water, dried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customat 93°-105° C.

Sources & evidence

ORD record
ord-9e6a455ca5cf4786a6fd3768f6e489fd
Source dataset
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04061656

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes