Acetone → HCID 15233469, compound

HRID 1492853Notes

Reaction equation

HRID 1492853 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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[CH:6][C:5]=1[OH:29].[C:31](=[O:34])([O-])[O-].[K+].[K+].[CH3:37][C:38]([CH3:40])=[O:39]>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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[CH:6][C:5]=1[O:29][CH2:16][CH2:15][CH2:14][O:39][C:38]1[CH:40]=[CH:11][C:12]([O:34][CH2:31][C:9]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:13][CH:37]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 15233482HCID 15233482, compound

Product 1

HCID 15233469HCID 15233469, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 g (2.4 mmol) of 2-hydroxy-5-(octadecyloxy) benzoic acid methyl ester, 0.85 g (2.6 mmol) of 3-[(4-phenylmethoxy)phenoxy]propyl bromide and 0.65 g (4.7 mmol) of potassium carbonate in 40 ml of acetone and 7 ml of DMF was stirred at reflux for 48 hours. The usual workup followed by recrystallization from ethyl acetate-hexane gave 1.2 g (76% yield, mp 81°-83°) of 5-(octadecyloxy)-2-[3-[4-(phenylmethoxy)phenoxy]propoxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe usual workup followed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5b8ef605634041079014671b2c32df70
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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