Methanol → HCID 53980466, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[OH:19])[C:5]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:6].[CH3:20]O>>[CH3:20][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([C:5](=[O:6])[C:4]2[CH:16]=[CH:17][C:18]([OH:19])=[C:2]([OH:1])[CH:3]=2)[CH:8]=1Participants
Procedure
A solution of 2.9g of 3-(3,4-dihydroxybenzoyl)-benzoic acid in 100 ml of methanol is mixed with 7g of Amberlyst 15® and refluxed with stirring for 8 hours. The reaction mixture is filtered on diatomaceous earth, the filtrate concentrated by evaporation, taken up in ethyl acetate and shaken out with 10% sodium bicarbonate solution. The organic phase is dried on sodium sulfate and concentrated by evaporation. 1.4g of 3-(3,4-dihydroxybenzoyl)-benzoic acid methyl ester is obtained as oily crude product. 272 mg of this crude product is dissolved in 2.5 ml of dimethylformamide, mixed with 269 mg of (1E)-6-bromo-l-(4-methoxyphenyl)-1-hexene and 185 mg of lithium carbonate and the mixture is heated for 18 hours to 50°-60° C. with stirring. The reaction mixture is filtered, washed with dichloromethane, the filtrate is concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate=98/2. 230 mg of 3-[3-hydroxy- 4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]benzoyl]-benzoic acid methyl ester is obtained as oil.
Workup
- temperaturerefluxed
- filtrationThe reaction mixture is filtered on diatomaceous earth
- concentrationthe filtrate concentrated by evaporation
- stirringshaken out with 10% sodium bicarbonate solution
- customThe organic phase is dried on sodium sulfate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-e51571d0e34044a291687ca19ea27160
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05352701
Reaction notes
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