Sodium Iodide → 3-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid methyl ester

HRID 1492863Notes

Reaction equation

HRID 1492863 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:5]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:31]=1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:31]=2[O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:7]=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 538683183-(Decyloxy)-5-hydroxybenzoic acid methyl ester

Product 1

HCID 538284933-(Decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid methyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (4.86 mmol) of 3-(decyloxy)-5-hydroxybenzoic acid methyl ester, 2.2 g (4.86 mmol) of 1-(6-bromohexyl)-2,3-bis (phenylmethoxy)benzene, 1.3 g (9.7 mmol) of potassium carbonate and 0.73 g (4.86 mmol) of sodium iodide in 50 ml of acetone and 15 ml of DMF was stirred at reflux for 48 hours. After the usual workup, the crude product was purified by HPLC using 10% ethyl acetate-hexane to give 2.47 g (75% yield, mp 45°-46°) of 3-(decyloxy)-5-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 48 hours
  2. customAfter the usual workup, the crude product was purified by HPLC

Sources & evidence

ORD record
ord-621238f32c7e44b3b44c0adb677f496d
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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