Diethyl Ether → 4-(4-octylphenyl)-3E-buten-2-one

HRID 1198218Notes

Reaction equation

HRID 1198218 reaction equation
[CH2:1]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O:19][CH2:20][CH3:21])C.[CH3:22]CCCCC>C1(C)C=CC=CC=1>[CH2:1]([C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:22]/[C:20](=[O:19])[CH3:21])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8058HexaneHCID 2734685Benzaldehyde, 4-octyl-

Product 1

HCID 191042884-(4-octylphenyl)-3E-buten-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triphenylphosporanylidene-2-propanone (2.9q, 0.o092 moles) and para-octylbenzaldehyde (2.0g, 0.0092 moles) in toluene (50ml) was heated to reflux for 2 hrs. and then stirred at room temperature for 64 hrs. The solution was poured into a solution of ethyl ether (100 ml) and hexane (100 ml). The white solid was removed by filtration and the filtrate concentrated by rotary evaporator to an oil. The title product was purified by silica gel chromatography. The structure assignment was supported by NMR, infrared spectra and elemental analysis (258.4).

Workup

  1. temperatureto reflux for 2 hrs
  2. customThe white solid was removed by filtration
  3. concentrationthe filtrate concentrated by rotary evaporator to an oil
  4. customThe title product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8c99186790ef4f5582ddebd159bcae4a
Source dataset
uspto-grants-1994_01
Patent number
US05280047

Reaction notes

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