p-Toluenesulfonic acid → HCID 549741, compound

HRID 465161Notes

Reaction equation

HRID 465161 reaction equation
[CH3:1][C:2]1[C:3](=[O:15])[CH2:4][CH2:5][C:6]([CH3:14])([CH3:13])[C:7]=1[C:8](=[O:12])[CH2:9][CH:10]=[CH2:11].C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:1][C:2]1[C:3](=[O:15])[CH2:4][CH2:5][C:6]([CH3:14])([CH3:13])[C:7]=1[C:8](=[O:12])[CH:9]=[CH:10][CH3:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 14676450HCID 14676450, compound

Product 1

HCID 549741HCID 549741, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

153 g (0.74 mole) of 2,4,4-trimethyl-3-(but-3-en-1-on-1-yl)-cyclohex-2-en-1-one (Ib) were stirred under reflux together with 135 ml of ethyl acetate and 3 g of p-toluenesulfonic acid for 2 hours. When the solution had cooled, 1,000 ml of ether were added to it, the mixture was washed with water and with saturated sodium bicarbonate solution and dried with sodium sulfate, and the solvent was distilled off under about 20 mbar. 153 g of 2,4,4-trimethyl-3-(but-2-en-1-on-1-yl)-cyclohex-2-en-1-one (Ia) were obtained, the yield being quantitative, and the product being only slightly impure according to thin-layer chromatography. Recristallization from 500 ml of cyclohexane gave 132 g (yield: 86.8% of theory) of a product which was pure according to thin-layer chromatography; evaporating down the mother liquor gave a further 21 g (yield: 13.2% of theory) of a somewhat impure product.

Workup

  1. temperatureWhen the solution had cooled
  2. washthe mixture was washed with water and with saturated sodium bicarbonate solution
  3. dry with materialdried with sodium sulfate
  4. distillationthe solvent was distilled off under about 20 mbar

Sources & evidence

ORD record
ord-9cbaf3977cc5449395feb11414c5affa
Source dataset
uspto-grants-1985_10
Patent number
US04550211

Reaction notes

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