Sodium Iodide → 4-[6-(2,3-Dimethoxyphenyl)hexyloxy]-3,5-dipropylbenzoic acid ethyl ester

HRID 1494224Notes

Reaction equation

HRID 1494224 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].[CH2:18]([O:20][C:21](=[O:35])[C:22]1[CH:27]=[C:26]([CH2:28][CH2:29][CH3:30])[C:25]([OH:31])=[C:24]([CH2:32][CH2:33][CH3:34])[CH:23]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:18]([O:20][C:21](=[O:35])[C:22]1[CH:27]=[C:26]([CH2:28][CH2:29][CH3:30])[C:25]([O:31][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:24]([CH2:32][CH2:33][CH3:34])[CH:23]=1)[CH3:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 57881Benzoic acid, 3,5-dipropyl-4-hydroxy-, ethyl esterHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzene

Product 1

HCID 149863234-[6-(2,3-Dimethoxyphenyl)hexyloxy]-3,5-dipropylbenzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.20 (4.0 mmol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene, 1.00 g (4.0 mmol) of 3,5-dipropyl-4-hydroxybenzoic acid ethyl ester, 1.10 g (8 mmol) of potassium carbonate and 0.6 g (4 mmol) of sodium iodide in 35 mL of acetone was stirred at reflux for 47 hours. Workup and purification as in Example 16 gave 4-[6-(2,3-dimethoxyphenyl)hexyloxy]-3,5-dipropylbenzoic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 47 hours
  2. customWorkup and purification as in Example 16

Sources & evidence

ORD record
ord-94daef12fe244f2380674374806925bd
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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