p-Toluenesulfonic acid → HCID 53812241, compound

HRID 1196176Notes

Reaction equation

HRID 1196176 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:4][CH:3]1[CH2:5][CH2:6][C:7]([CH3:14])=[C:8]=[CH:9][CH2:10][C:11](=[O:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C1(C)C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:15])[CH2:4][CH:3]1[CH2:5][CH2:6][C:7]([CH3:14])=[CH:8][CH:9]=[CH:10][C:11](=[O:13])[CH3:12]

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57114791HCID 57114791, compound

Product 1

HCID 53812241HCID 53812241, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

8-(2',2'-Dimethylcyclopropyl)-6-methyl-4,5-octadien-2-one, 5 g, is dissolved in a mixture of 6 ml of methanol and 6 ml of toluene, then 200 mg of p-toluenesulphonic acid are added. The mixture is stirred at room temperature for 63/4 hours. It is diluted with ether, washed neutral with saturated bicarbonate and carbonate solution and with saturated sodium chloride solution, dried and concentrated. The crude product (4.5 g) is distilled in a bulb-tube. In this manner there are obtained 4.2 g (84%) of 8-(2',2'-dimethyl-cyclopropyl)-6-methyl-3,5-octadien-2-one. EZ/EE=4/6.

Workup

  1. washwashed neutral with saturated bicarbonate and carbonate solution and with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. distillationThe crude product (4.5 g) is distilled in a bulb-tube

Sources & evidence

ORD record
ord-a77e7f1e7f9c4f67b9905c4543df7b03
Source dataset
uspto-grants-1992_05
Patent number
US05113021

Reaction notes

Loading…