Potassium Carbonate → HCID 53921746, compound

HRID 1492852Notes

Reaction equation

HRID 1492852 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:37](=[O:40])([O-])[O-].[K+].[K+].[C:43]([O:46][CH2:47][CH3:48])(=O)[CH3:44].[CH3:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:11]=[C:12]([O:35][CH2:9][CH2:10][CH2:11][CH2:12][CH2:48][CH2:47][O:46][C:43]3[CH:44]=[CH:3][C:2]([O:40][CH2:37][C:51]4[CH:50]=[CH:49][CH:54]=[CH:53][CH:52]=4)=[CH:1][CH:6]=3)[CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl esterHCID 21226206Ethyl acetate hexane

Product 1

HCID 53921746HCID 53921746, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.60 (1.2 mmol) of 3-hydroxy-5-(octadecyloxy) benzoic acid phenylmethyl ester, 0.46 g (1.27 mmol) of 6-[(4-phenylmethoxy)phenoxy]hexyl bromide and 0.3 g (2.17 mmol) of potassium carbonate in 20 ml of acetone and 1 ml of DMF was stirred at reflux for 21 hours. The usual workup followed by chromatography on 40 g of silica gel (230-400 mesh) using 5% ethyl acetate-hexane gave 0.7 g (74% yield, mp 60°-62°) of 3-(octadecyloxy)-5-[[6-[4-(phenylmethoxy)phenoxy]hexyl]oxy]benzoic acid phenylmethyl ester.

Workup

  1. temperatureat reflux for 21 hours

Sources & evidence

ORD record
ord-a232d126b7734cc5ade3784edf8de606
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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