Sodium Iodide → 4-[6-[2,3-Bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl ester

HRID 1494263Notes

Reaction equation

HRID 1494263 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][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[CH3:31].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:30]([O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][C:37]([O:40][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][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:36][CH:35]=1)[CH3:31]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzene

Product 1

HCID 149864454-[6-[2,3-Bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.4 g (5.3 mmole) of 1-(6-bromohexyl)-2,3-bis-(phenylmethoxy)benzene, 0.88 g (5.3 mmole) of 4-hydroxybenzoic acid ethyl ester, 2.5 g (18 mmole) of potassium carbonate and 0.8 g (5.3 mmole) of sodium iodide in 40 mL of acetone was stirred at reflux for 22 hours. Workup as in Example 16 and recrystallization of the crude product from ethyl acetate-hexane gave 2.3 g, mp 63°-65° (81% yield) of 4-[6-[2,3-bis(phenylmethoxy)phenyl]hexyloxy]benzoic acid ethyl ester.

Workup

  1. temperatureat reflux for 22 hours
  2. customWorkup as in Example 16 and recrystallization of the crude product from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ebbec42f6f9848e0bbd0febb5d7bd1c2
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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