Potassium Carbonate → HCID 14986412, compound

HRID 1494253Notes

Reaction equation

HRID 1494253 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=1[CH3:20])=[O:8].[CH3:21][O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:31][CH2:32][CH3:33])[C:25]=1[OH:34].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:21][O:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=2[CH3:20])=[O:8])=[C:26]([CH2:31][CH2:32][CH3:33])[C:25]=1[OH:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoateHCID 14986401HCID 14986401, compound

Product 1

HCID 14986412HCID 14986412, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.50 g (7.29 mmol) of 6-bromo-1-(3,4-dimethoxy-2,5-dimethylphenyl)-1-hexanone, 1.53 g (7.29 mmol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester and 3.30 g (24 mmol) of potassium carbonate in 50 mL of acetone and 5 mL of DMF was stirred and heated at reflux for 26 hours. After workup as in Example 16 the crude product was purified by HPLC using 10% ethyl acetate-hexane to give 3.40 g (98% yield) of 4-[[6-(3,4-dimethoxy-2,5-dimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propyl benzoic acid methyl ester as an oil. The nmr spectrum was consistent with the structure.

Workup

  1. temperatureheated
  2. temperatureat reflux for 26 hours
  3. customAfter workup as in Example 16 the crude product was purified by HPLC

Sources & evidence

ORD record
ord-e68f5c2a42fb434083ae718e9f9609fd
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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