Diethylene glycol monophenyl ether → HCID 54457781, compound

HRID 2225678Notes

Reaction equation

HRID 2225678 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.[C:21]1([O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32]O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7715Diethylene glycol monophenyl etherHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54457781HCID 54457781, compoundYield 65%

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 diethyleneglycol monophenyl ether (1.56 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-ethyl acetate; 50:1) and crystallized from dichloromethane-hexane to provide 0.9 g of 4-[[2-[[2-(phenoxy)ethyl]oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 75°-76° C.

Workup

  1. customThe material was purified by HPLC (dichloromethane-ethyl acetate; 50:1)
  2. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-364abd5d33f743a09c1cbf9141fa2bc0
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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