2-(2-Naphthoxy)ethanol → 4-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225685Notes

Reaction equation

HRID 2225685 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.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[O:31][CH2:32][CH2:33]O>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][CH2:33][CH2:32][O:31][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 71312-(2-Naphthoxy)ethanolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl esterYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (3.62 g) in dimethylformamide (40 mL) under argon was treated with 55% sodium hydride (0.875 g), stirred for 15 minutes and treated with the mesylate of 2-(2-naphthyloxy)ethanol (5.48 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was crystallized from dichloromethane-hexane to provide 4.2 g of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 155°-157° C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-adf7dccdc4b649e88a9b2cb1c6ee832a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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