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

HRID 1613050Notes

Reaction equation

HRID 1613050 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:32])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([CH2:29][CH2:30][CH3:31])[CH:23]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:18]([O:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([O:28][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]([CH2:29][CH2:30][CH3:31])[CH:23]=1)[CH3:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzeneHCID 14986319Ethyl 4-hydroxy-3-propylbenzoate

Product 1

HCID 149863204-[6-(2,3-Dimethoxyphenyl)hexyloxy]-3-propylbenzoic acid ethyl esterYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.40 g (4.8 mmol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene, 1.00 g (4.8 mmol) of 4-hydroxy-3-propylbenzoic acid ethyl ester, 1.30 g (9.6 mmol) of potassium carbonate and 0.72 g (4.8 mmol) of sodium iodide in 35 mL of acetone was stirred at reflux for 47 hours. Workup and purification as described in Example 16 gave 2.0 g of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]-3-propylbenzoic acid ethyl ester as an oil. The mass spectrum showed the molecular ion at m/e 428.

Workup

  1. temperatureat reflux for 47 hours
  2. customWorkup and purification

Sources & evidence

ORD record
ord-e002763901344fc08e45656d420fdf58
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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