Potassium Carbonate → 5-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester

HRID 488322Notes

Reaction equation

HRID 488322 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11].[C:13]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:18][CH:17]=2)[CH:7]=[CH:6][C:5]=1[OH:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75077Methyl GentisateHCID 234323996-([1,1'-Biphenyl]-4-yloxy)hexyl bromide

Product 1

HCID 545134655-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl esterYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (6 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 2.0 g (6 mmol) of 6-([1,1'-biphenyl]-4-yloxy)hexyl bromide and 1.24 g (9 mmol) of potassium carbonate in 50 ml of acetone and 5 ml of DMF was stirred at reflux for 27 hours. The solvents were removed at reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by chromatography on 40 g of silica gel using 50% toluene-hexane to give 1.4 g (56% yield, mp 91°-92°) of 5-[[6-([1,1'-biphenyl]4-yloxy)hexyl]oxy]-2-hydroxybenzoic acid methyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux for 27 hours
  2. customThe solvents were removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by chromatography on 40 g of silica gel using 50% toluene-hexane

Sources & evidence

ORD record
ord-a19262170b614899affda64e2eb4271a
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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