p-Toluenesulfonic acid → Cyclohexanone, 3,3-dimethyl-

HRID 1189726Notes

Reaction equation

HRID 1189726 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=O)[CH2:6][C:4](=[O:5])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Pd].C(O)(C)C>[CH3:1][C:2]1([CH3:10])[CH2:9][CH2:7][CH2:6][C:4](=[O:5])[CH2:3]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 31358Dimedone

Product 1

HCID 76322Cyclohexanone, 3,3-dimethyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

41 g of 5% Pd/C E 101 N/D were placed in a 2 L glass-steel autoclave with glass-liner. 385 g of dimedone (2.75 mol), 663 g (850 mL) of isopropanol and 15.3 g (88 mmol) of p-toluene sulfonic acid were added. The glass-liner was closed and stirring was started with 500 rpm. The autoclave was flushed three times with 5 bara N2. The stirrer was turned off. The autoclave was then pressurized with 5 bara H2 for 10 minutes for pressure check. The pressure was released.

Workup

  1. customThe glass-liner was closed
  2. customThe autoclave was flushed three times with 5 bara N2

Sources & evidence

ORD record
ord-1a166b49ab284d229e7c122aa23caa0c
Source dataset
uspto-grants-2014_03
Patent number
US08674143B2

Reaction notes

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