Butanoic acid, 4-chloro-4-oxo-, methyl ester → 4-(3,4-Diethoxy-phenyl)-4-oxo-butyric acid methyl ester

HRID 1983992Notes

Reaction equation

HRID 1983992 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH2:5][C:6](Cl)=[O:7].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24][CH3:25])[CH3:15]>ClCCl>[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH2:5][C:6]([C:21]1[CH:20]=[CH:19][C:18]([O:23][CH2:24][CH3:25])=[C:17]([O:16][CH2:14][CH3:15])[CH:22]=1)=[O:7]

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 74904o-DiethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 577140984-(3,4-Diethoxy-phenyl)-4-oxo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.1 A solution of 70 ml 3-chlorocarbonyl-propionic acid methyl ester in 100 ml dichloromethane is added to a suspension of 80.0 g of AlCl3 in 300 ml dichloromethane at 20-25°. At 0° a solution of 85.0 g 1,2-diethoxybenzene in 100 ml dichloromethane is added. The solution is tirred for 14 hours at room temperature. Work-up is as usual, yielding 122.2 g of 4-(3,4-diethoxy-phenyl)-4-oxo-butyric acid methyl ester (“AA”), m.p. 84-85°.

Sources & evidence

ORD record
ord-775459e4bbda44d7874e9c00b11fe8a0
Source dataset
uspto-grants-2009_06
Patent number
US07544684B2

Reaction notes

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