Hydrochloric Acid → 4-Methoxy-gamma-oxobenzenebutanoic acid

HRID 846215Notes

Reaction equation

HRID 846215 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.[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCCCl.O>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Anisole (70.0 g) and succinic anhydride (65.0 g) were dissolved in 1,2-dichloroethane (1 liter) and the mixture was cooled to 0° C. To the resulting suspension there was added, in portions, AlCl3 (172 g) and the resulting mixture was stirred with a mechanical stirrer for 1 hour. The mixture was then poured into a mixture of ice and water (about 1 liter) containing 50 ml of concentrated HCl. The resulting white solid was collected by filtration, washed with water and air-dried to yield 4-methoxy-gamma-oxobenzenebutanoic acid, mp 145°-147° C.

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-c4c543bec449489abfdf06e2d206d405
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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