p-Toluenesulfonic acid → 2,4-Dimethyl-3-cyclohexene carboxaldehyde

HRID 1681807Notes

Reaction equation

HRID 1681807 reaction equation
CC(C(CC)C)(CO)[CH2:3][OH:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.C[C:23]1[CH2:24][CH:25]([CH:30]=O)[CH2:26][CH:27]([CH3:29])[CH:28]=1>C1CCCCC1>[CH3:29][CH:27]1[CH:28]([CH:3]=[O:4])[CH2:23][CH2:24][C:25]([CH3:30])=[CH:26]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 978543,5-Dimethyl-3-cyclohexene carboxaldehydeHCID 980761,3-Propanediol, 2-methyl-2-(1-methylpropyl)-

Product 1

HCID 933752,4-Dimethyl-3-cyclohexene carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A 3-necked round bottom flask (250 ml capacity) was fitted with a mechanical stirrer, thermometer and Dean and Stark apparatus, the latter was equipped with a double surface water condenser. Privetal (0.1 mole, 14.6 g) and 2-methyl-2-sec.butylpropane-1,3 diol (0.1 mole 14.6 g) were charged into the flask together with cyclohexane (50 ml) as solvent and a catalytic amount of p-toluenesulphonic acid (0.35 g). Privetal was a mixture of 2,4-dimethyl-and 3,5-dimethyl-cyclohex-3-ene-1-carboxaldehyde obtained from PPF International, Ashford, England; now obtained under the trade name Ligustral from Quest International, Ashford, Kent the successor company to PPF International. (The 1,3-diol was obtained from Hoechst GmbH of West Germany.)

Workup

  1. customA 3-necked round bottom flask (250 ml capacity) was fitted with a mechanical stirrer
  2. customthermometer and Dean and Stark apparatus, the latter was equipped with a double surface water condenser

Sources & evidence

ORD record
ord-c12154f0373b461d85c1c52680fb5f74
Source dataset
uspto-grants-1992_12
Patent number
US05175143

Reaction notes

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