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

HRID 1494232Notes

Reaction equation

HRID 1494232 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:29])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[OH:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:18][O:19][C:20](=[O:29])[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][C:22]=1[OH:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzene

Product 1

HCID 149863384-[6-(2,3-Dimethoxyphenyl)hexyloxy]-2-hydroxybenzoic acid methyl esterYield 93.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.0 g (3.3 mmol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene, 0.55 g (3.3 mmol) of 2,4-dihydroxybenzoic acid methyl ester, 1.2 g (9 mmol) of potassium carbonate and 0.75 g (4.5 mmol) of potassium iodide in 25 mL of acetone was stirred at reflux for 20 hours. Workup as in Example 16 gave 1.2 g of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]-2-hydroxybenzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 20 hours

Sources & evidence

ORD record
ord-127a9b5db86f429ea3ebe42756341005
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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