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

HRID 1613048Notes

Reaction equation

HRID 1613048 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:32])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH2:28][CH2:29][CH3:30])[C:22]=1[OH:31].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:18][O:19][C:20](=[O:32])[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])=[C:23]([CH2:28][CH2:29][CH3:30])[C:22]=1[OH:31]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoateHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzene

Product 1

HCID 149862944-[6-(2,3-Dimethoxyphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 29.2 g (0.097 mol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene, 18.5 g (0.088 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester, 18.2 g (0.13 mol) of anhydrous potassium carbonate and 21.9 g (0.13 mol) of potassium iodide in 550 mL of anhydrous acetone was stirred at reflux for 22 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to an oil which was purified by HPLC using 8% ethyl acetate-hexane to give 31.4 g (83% yield) of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]-2-hydroxy-3-propylbenzoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 22 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to an oil which
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-60f397b89c4545908f6e24c9e437bc63
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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