Potassium Carbonate → 3,4-Bis(heptyloxy)benzoic acid methyl ester

HRID 1728879Notes

Reaction equation

HRID 1728879 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.I[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:6]([O:11][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 202741-IodoheptaneHCID 287064Methyl 3,4-Dihydroxybenzoate

Product 1

HCID 540951973,4-Bis(heptyloxy)benzoic acid methyl esterYield 198.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 25 g of product from Example 102, 72.3 g of 1-iodoheptane, 61.65 g of potassium carbonate and 500 ml of 2-butanone is heated at reflux temperature for 44 hours. The cooled reaction mixture is filtered and concentrated in vacuo. The oily residue is purified by chromatography (silica gel: 10% ethyl acetate/hexane) to give 53.7 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 44 hours
  3. customThe cooled reaction mixture
  4. filtrationis filtered
  5. concentrationconcentrated in vacuo
  6. customThe oily residue is purified by chromatography (silica gel: 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-182f5e2043b043859d56c1beb1ae2ee7
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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