Potassium Carbonate → 4-[[6-(3,4-Dimethoxy-2,5,6-trimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester

HRID 1613082Notes

Reaction equation

HRID 1613082 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[C:10]=1[CH3:21])=[O:8].[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[C:10]=2[CH3:21])=[O:8])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoateHCID 149864296-Bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-1-hexanone

Product 1

HCID 149864304-[[6-(3,4-Dimethoxy-2,5,6-trimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl esterYield 83%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.194 g (2.6 mmol) of 6-bromo-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-1-hexanone, 0.55 g (2.6 mmol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester and 1.10 g (7.8 mmol) of potassium carbonate in 20 mL of acetone and 2 mL of DMF was stirred at reflux for 17 hours. After workup as in Example 16, the crude product was purified by chromatography on 100 g of silica gel. Elution with 10% ethyl acetate-hexane gave 1.05 g (83% yield) of 4-[[6-(3,4-dimethoxy-2,5,6-trimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester. The nmr spectrum was consistent with the structure and the mass spectrum gave the molecular ion at m/z 486 (C28H28O7).

Workup

  1. temperatureat reflux for 17 hours
  2. customAfter workup as in Example 16, the crude product was purified by chromatography on 100 g of silica gel
  3. washElution with 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-266eb13642904cd4996b6b06592928f8
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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