(3-Bromopropyl)benzene → HCID 54243338, compound

HRID 2225631Notes

Reaction equation

HRID 2225631 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+].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54243338HCID 54243338, compound

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 3-bromo-1-phenylpropane. The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-hexane; 4:1) to provide 0.65 g of 4-[(3-phenylpropyl)oxy]-alpha-oxobenzeneacetic acid methyl ester as a colorless oil.

Workup

  1. customThe material was purified by HPLC (dichloromethane-hexane; 4:1)

Sources & evidence

ORD record
ord-6ccb4170d3c54b60af35ac88b26d9675
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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