2-(4-Chlorophenoxy)ethanol → 4-[[2-(4-Chlorophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225651Notes

Reaction equation

HRID 2225651 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.[Cl:21][C:22]1[CH:31]=[CH:30][C:25]([O:26][CH2:27][CH2:28]O)=[CH:24][CH:23]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:28][CH2:27][O:26][C:25]2[CH:30]=[CH:31][C:22]([Cl:21])=[CH:23][CH:24]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 159072-(4-Chlorophenoxy)ethanolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 544487314-[[2-(4-Chlorophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl esterYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the mesylate of 2-(4-chlorophenoxy)ethanol (1.25 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 4:1 ) and crystallized from dichloromethane-hexane to provide 0.815 g of 4-[[2-(4-chlorophenoxy) ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 103°-105° C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (dichloromethane-hexane; 4:1 )
  3. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-7d6b3847719647b3be367bc4cd48ee7c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…