p-Toluenesulfonic acid → HCID 11019364, compound

HRID 2295195Notes

Reaction equation

HRID 2295195 reaction equation
O[CH:2]([CH:12]([CH3:14])[CH3:13])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[CH3:13][CH:12]([CH3:14])/[CH:2]=[CH:3]/[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 9834191HCID 9834191, compound

Product 1

HCID 11019364HCID 11019364, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-hydroxy-4-methyl-1-phenyl-1-pentanone (8.400 gm, 43.7 mmol) and p-toluenesulfonic acid (820 mg, 4.3 mmol) in benzene (210 ml) was refluxed in a Dean-Stark apparatus for 10 minutes. The solution was cooled, diluted with Et2O, and washed with saturated NaHCO3 and brine. Filtration and removal of the solvent afforded a yellow oil which was subsequently distilled (P=2.0 mm, 97°-100° C.) to give the (E)-4-methyl-1-phenyl-2-penten-1-one (6.94 gm) as a colorless liquid. 1H-NMR analysis showed the distillate to be 78% the desired product and 22% the β, δ-unsaturated isomer. The material was used directly for the next reaction.

Workup

  1. temperaturewas refluxed in a Dean-Stark apparatus for 10 minutes
  2. temperatureThe solution was cooled
  3. washwashed with saturated NaHCO3 and brine
  4. filtrationFiltration and removal of the solvent
  5. customafforded a yellow oil which
  6. distillationwas subsequently distilled (P=2.0 mm, 97°-100° C.)

Sources & evidence

ORD record
ord-f42ec3e5ecf247ed8d3e86d95e86adb3
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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