p-Toluenesulfonic acid → 1-(1,1-Dimethoxyethyl)-4-(4,4-dimethylcyclohex-1-enyl)benzene

HRID 1018803Notes

Reaction equation

HRID 1018803 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH2:3]1.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:29][O:30]C(OC)OC>CO.C(OC(C)C)(C)C>[CH3:18][O:16][C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH2:6][CH2:7][C:2]([CH3:17])([CH3:1])[CH2:3][CH:4]=2)=[CH:13][CH:12]=1)([O:30][CH3:29])[CH3:15]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 184025021-[4-(4,4-Dimethylcyclohex-1-enyl)phenyl]ethanone

Product 1

HCID 184024991-(1,1-Dimethoxyethyl)-4-(4,4-dimethylcyclohex-1-enyl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

36.13 g of 1-[4-(4,4-dimethylcyclohex-1-enyl)phenyl]ethanone (compound VI.1) in 250 ml of methanol are stirred for 12 hours at room temperature in the presence of 0.5 g of para-toluenesulphonic acid (PTSA) and 13 ml of trimethyl-ortho-formate. The solvents are partially evaporated off under reduced pressure. A 50% solution of potassium hydroxide in methanol is added and the solvents are then evaporated off under reduced pressure. The residue obtained is taken up in diisopropyl ether and the solvent is then evaporated off under reduced pressure.

Workup

  1. customThe solvents are partially evaporated off under reduced pressure
  2. additionA 50% solution of potassium hydroxide in methanol is added
  3. customthe solvents are then evaporated off under reduced pressure
  4. customThe residue obtained
  5. customthe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-d08d0d730ca64722896b6e9b3405be46
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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