1-Bromooctadecane → HCID 15233467, compound

HRID 1492845Notes

Reaction equation

HRID 1492845 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([OH:29])[CH:5]=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH:7]=[C:6]([O:29][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH3:32])[CH:5]=1

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 54194410HCID 54194410, compound

Product 1

HCID 15233467HCID 15233467, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11 g (27 mmol) of 3-hydroxy-5-[3-[4-(phenyl-methoxy)phenoxy]propoxy]benzoic acid methyl ester, 9.9 g (29.6 mmol) of 1-bromooctadecane and 7.5 g (55 mmol) of potassium carbonate in 225 ml of DMF was stirred and heated at 80° for 30 hours. The solvent was removed at reduced pressure and the residue was purified by chromatography on 300 g of silica gel using 10% ethyl acetate-hexane to give 15.7 g (88% yield, mp 76°-77°) of 3-(octadecyloxy)-5-[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester.

Workup

  1. temperatureheated at 80° for 30 hours
  2. customThe solvent was removed at reduced pressure
  3. customthe residue was purified by chromatography on 300 g of silica gel using 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-8bc1e3daef654f6ea2f860876b46ebcb
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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