Hydrochloric Acid → 3-(4-Hydroxy-3-methoxybenzoyl)-benzoic acid methyl ester

HRID 1707289Notes

Reaction equation

HRID 1707289 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([O:13]C)[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=1)[O:7][CH3:8].[Cl-].[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH:27]=[CH:26][CH:25]=[C:21]([C:22](O)=[O:23])[CH:20]=1.Cl>ClCCl>[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH:27]=[CH:26][CH:25]=[C:21]([C:22](=[O:23])[C:10]2[CH:11]=[CH:12][C:5]([OH:13])=[C:6]([O:7][CH3:8])[CH:9]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 6451240Aluminum(III) ChlorideHCID 86748168Isophthalic acid monomethyl ester chloride

Product 1

HCID 545284813-(4-Hydroxy-3-methoxybenzoyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

14.8g of aluminum chloride and 5g of veratrole are added to a solution of 7.34g of isophthalic acid monomethyl ester chloride in 160 ml of dichloromethane under ice cooling. The reaction mixture is refluxed for 8 hours, poured on ice water, acidified with 2 n of hydrochloric acid and shaken out with dichloromethane. The organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate=8/2. 3.5g of 3-(4-hydroxy-3-methoxybenzoyl)-benzoic acid methyl ester of melting point of 133°-134° C. is obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 8 hours
  2. additionpoured on ice water
  3. customThe organic phase is dried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customthe residue is chromatographed on silica gel with hexane/ethyl acetate=8/2

Sources & evidence

ORD record
ord-d3c20145b57d4abfa74c43bec6cc88f6
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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