Sodium hydride → alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester

HRID 488332Notes

Reaction equation

HRID 488332 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:4].[O:17]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:10][CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 1236990412-Phenoxydodecyl bromide

Product 1

HCID 54340854alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.162 g (4.06 mmol) of 60% sodium hydride on oil in 10 ml of anhydrous DMF was added 0.75 g (3.87 mmol) of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester. The reaction mixture was stirred at room temperature under argon for 15 minutes and then 1.4 g (4.06 mmol) of 12-phenoxydodecyl bromide in 20 ml of anhydrous DMF was added. The mixture was stirred and heated at 60° for 24 hours. The usual workup followed by chromatography on 45 g of silica gel gave alpha-oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester (83% yield, mp 58°-59°).

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated at 60° for 24 hours

Sources & evidence

ORD record
ord-29cce4df8a7746a181c54d04b5dbfd88
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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