Potassium Iodide → 4-[6-(2,3-Dimethoxyphenyl)hexyloxy]benzoic acid methyl ester

HRID 1494236Notes

Reaction equation

HRID 1494236 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[O:16][CH3:17].[CH3:18][O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:18][O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=2[O:16][CH3:17])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzene

Product 1

HCID 149863444-[6-(2,3-Dimethoxyphenyl)hexyloxy]benzoic acid methyl esterYield 98.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.00 g (3.3 mmol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene, 0.45 g (3.0 mmol) of 4-hydroxybenzoic acid methyl ester, 0.62 g (4.5 mmol) of potassium carbonate and 0.75 g (4.5 mmol) of potassium iodide in 25 mL of acetone was stirred at reflux for 23 hours. Workup as in Example 16 and purification by HPLC using 15% ethyl acetate-hexane gave 1.10 g (89% yield) of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]benzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 23 hours
  2. customWorkup as in Example 16 and purification by HPLC

Sources & evidence

ORD record
ord-918026801c90482796f39eb97fc7fbe2
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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