Methanol → 5-(3,4-Dihydroxyphenyl)-5-oxo-pentanoic acid methyl ester

HRID 1707298Notes

Reaction equation

HRID 1707298 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:17]O>>[CH3:17][O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:9]([C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)=[O:16]

Participants

3

Reactant 2

HCID 887MethanolHCID 189630805-(3,4-Dihydroxyphenyl)-5-oxopentanoic acid

Product 1

HCID 231781405-(3,4-Dihydroxyphenyl)-5-oxo-pentanoic acid methyl ester

Procedure

A solution of 5.6g of 5-(3,4-dihydroxyphenyl)-5-oxopentanoic acid in 300 ml of methanol is stirred together with 15g of Amberlyst 15 for 16 hours at room temperature. The reaction mixture is filtered on diatomaceous earth, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate (20-60%). 3.7 g of 5-(3,4-dihydroxyphenyl)-5-oxo-pentanoic acid methyl ester of melting point 104°-106° C. is obtained.

Workup

  1. filtrationThe reaction mixture is filtered on diatomaceous earth
  2. concentrationconcentrated by evaporation
  3. customthe residue is chromatographed on silica gel with hexane/ethyl acetate (20-60%)

Sources & evidence

ORD record
ord-f08fef406bd947cbb6dd38c2b071d960
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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