Sodium Hydroxide → 4-(2-Nonyloxyphenyl)-3-butene-2-one

HRID 868487Notes

Reaction equation

HRID 868487 reaction equation
[CH2:1]([O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH-].[Na+].C([O:24][CH2:25][CH3:26])(=O)C.[CH3:27]CCCCC>CC(C)=O.[Cl-].[Na+].O>[CH2:1]([O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[CH:27][C:25](=[O:24])[CH3:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 13785718HCID 13785718, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 540771084-(2-Nonyloxyphenyl)-3-butene-2-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(nonyloxy)benzaldehyde (62 g) dissolved in acetone (500 mL) was treated with aqueous sodium hydroxide (100 mL, 1M) at room temperature for 18 h. Brine and ethyl acetate/hexane (1:1 parts by volume) was then added. Concentration of the organic phase followed by crystallization from hexane gave 4-(2-nonyloxyphenyl)-3-butene-2-one (53 g).

Workup

  1. customConcentration of the organic phase followed by crystallization from hexane

Sources & evidence

ORD record
ord-4dac9e35efda490286c505b9585514ee
Source dataset
uspto-grants-1988_10
Patent number
US04780251

Reaction notes

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