Homogentisic Acid → 2',5'-Dimethoxyacetophenone

HRID 2051722Notes

Reaction equation

HRID 2051722 reaction equation
C(O)(=O)C[C:3]1[C:4](=CC=C(C=1)O)[OH:5].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(Cl)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:3][C:4]([C:19]1[CH:20]=[C:15]([O:14][CH3:13])[CH:16]=[CH:17][C:18]=1[O:21][CH3:22])=[O:5]

Participants

5

Reactant 4

HCID 780Homogentisic AcidHCID 6367Acetyl chlorideHCID 90161,4-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 709912',5'-Dimethoxyacetophenone

Procedure

The best method known for preparing homogentisic acid appears to be that described in J. Biol. Chem. 179, 365 (1949), in which 1,4-dimethoxybenzene is reacted with acetyl chloride in the presence of aluminum chloride to give 2,5-dimethoxyacetophenone, the latter is reacted with sulphur in morpholine to give 2,5-dimethoxyphenylacetic acid, which on demethylation with hydrobromic acid gives homogentisic lactone, ring-opening of which gives the desired acid.

Sources & evidence

ORD record
ord-f90bd63bf389483db5ca0a9c6b7c36e2
Source dataset
uspto-grants-1980_01
Patent number
US04182720

Reaction notes

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