Hydrochloric Acid → 4-Methoxy-gamma-oxobenzenebutanoic acid

HRID 1360210Notes

Reaction equation

HRID 1360210 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([O:11][CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:13]1(=[O:19])[O:18][C:16](=[O:17])[CH2:15][CH2:14]1.Cl>C(OCC)(=O)C.C(Cl)Cl>[CH3:12][O:11][C:5]1[CH:10]=[CH:9][C:8]([C:13](=[O:19])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:7][CH:6]=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 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methylene chloride (300 ml) was added to aluminum chloride (185.6 g) and anisole (100 ml) was added dropwise thereto at 0° C. Succinic anhydride (100 g) was added thereto in 5 portions and the resulting mixture was warmed up to room temperature and stirred for 3 hours. The reaction solution was added to a 4N aqueous hydrochloric acid solution (2 L) and ethyl acetate (1 L) under ice-cooling, and the crystals precipitated were collected by filtration and dried to obtain 4-(4-methoxyphenyl)-4-oxobutanoic acid (160 g) as a white solid.

Workup

  1. additionwas added dropwise
  2. customat 0° C
  3. temperaturecooling
  4. customthe crystals precipitated
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-673282989a18404ca83ae9846b5bda5f
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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