Anisole → 4-Methoxy-gamma-oxobenzenebutanoic acid

HRID 860844Notes

Reaction equation

HRID 860844 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7519AnisoleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 766134-Methoxy-gamma-oxobenzenebutanoic acidYield 84.6%

Procedure

The title compound was prepared from anisole (11 g, 102 mmol) and succinic anhydride (i2 g, 120 m mol) in presence of anhydrous aluminum chloride (30 g) by the same method as described for 2 above to furnish 4-(4-methoxyphenyl)-4-oxo-butanoic acid in 84.6% yield, which on purification and crystallization from methanol/ethyl acetate (1:9) produced white crystals of 3, mp142–43° C., analyzed for C11,H12, O4 (found C64.21, H5.86; requires C63.45, H5.80%).

Sources & evidence

ORD record
ord-1397d5b4d9e744a59ec94ddc1b3b105a
Source dataset
uspto-grants-2006_12
Patent number
US07153983B2

Reaction notes

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