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

HRID 1492860Notes

Reaction equation

HRID 1492860 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=[C:6]([OH:25])[CH:5]=1.Br[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:35]=1[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=[C:6]([O:25][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:35]=2[O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneHCID 152334833-Hydroxy-5-(tetradecyloxy)benzoic acid methyl ester

Product 1

HCID 152334703-[[6-[2,3-Bis(phenylmethoxy)phenyl]hexyl]oxy]-5-(tetradecyloxy) benzoic acid methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (4.1 mmol) of 3-hydroxy-5-(tetradecyloxy) benzoic acid methyl ester, 2.3 g (5.1 mmol) of 1-(6-bromohexyl)-2,3-bis(phenylmethoxy)benzene, 1.1 g (8.2 mmol) of potassium carbonate and 0.6 g (4.1 mmol) of sodium iodide in 50 ml of acetone and 15 ml of DMF was stirred at reflux under argon for 32 hours. After the usual workup, the crude product was crystallized from methylene chloride-methanol to give 2.8 g (93% yield, mp 56°-58°) of 3-[[6-[2,3-bis(phenylmethoxy)phenyl]hexyl]oxy]-5-(tetradecyloxy) benzoic acid methyl ester.

Workup

  1. temperatureat reflux under argon for 32 hours
  2. customAfter the usual workup, the crude product was crystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-7366c2a311b3436992aa72d17471cae4
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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