4-Methoxybenzaldehyde → HCID 70588710, compound

HRID 1449008Notes

Reaction equation

HRID 1449008 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])=O)[CH3:12].[CH2:24]([O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])[CH3:25]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:7]([C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:28]([C:27]([O:26][CH2:24][CH3:25])=[O:32])=[C:29]([CH3:30])[NH:31][C:16]=1[CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:23])[CH3:12]

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 70588710HCID 70588710, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After heating a solution of 5.7 g of 4-methoxybenzaldehyde, 7.9 g of γ-acetoxyacetoacetic acid ethyl ester and 5.5 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol for 20 hours, the mixture is cooled and the precipitate is filtered off and recrystallised from ether. White crystals of melting point 89°-90° C., yield: 45%

Workup

  1. temperaturethe mixture is cooled
  2. filtrationthe precipitate is filtered off
  3. customrecrystallised from ether

Sources & evidence

ORD record
ord-5a9cc61a1a1946fda716734cc8f98848
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

Loading…