Dichloromethane → 3-(3-Ethoxy-3-oxopropyl)-4-methoxy-gamma-oxobenzenebutanoic Acid

HRID 328002Notes

Reaction equation

HRID 328002 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH3:2].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 578401Ethyl 3-(2-methoxyphenyl)propanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 199220913-(3-Ethoxy-3-oxopropyl)-4-methoxy-gamma-oxobenzenebutanoic AcidYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with a mixture of 3.12 g (15.0 mmol) of 2-methoxybenzenepropanoic acid ethyl ester, 1.53 g (15.3 mmol) of succinic anhydride, 4.46 (33.5 mmol) of aluminum chloride and 20 mL of methylene chloride, the title compound (3.59 g, 77.7%) was obtained as a white solid, mp 128°-129° C. (recrystallized from ethanol), using the procedure of example 139.

Sources & evidence

ORD record
ord-0e8530a8b4a04265b8d474db93a33913
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

Loading…