Epichlorohydrin → HCID 53978224, compound

HRID 2225680Notes

Reaction equation

HRID 2225680 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+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>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][CH2:16][CH:18]2[CH2:19][O:20]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 53978224HCID 53978224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (2.71 g) in dimethylformamide (20 mL) under argon was treated with 55% sodium hydride (0.65 g) , stirred for 15 minutes and treated with epichlorohydrin (12 mL). The mixture was heated at 60° C. for four hours and worked up as in Example 20. The material was purified by HPLC (dichloromethane-diethyl ether; 50:1) to provide 2.4 g of 4-(oxiranylmethoxy)alpha-oxobenzeneacetic acid methyl ester, as an oil.

Workup

  1. customThe material was purified by HPLC (dichloromethane-diethyl ether; 50:1)

Sources & evidence

ORD record
ord-9c2d4de02f1e474596907008864b0dbc
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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