p-Toluenesulfonic acid → HCID 21904108, compound

HRID 1246583Notes

Reaction equation

HRID 1246583 reaction equation
[C:1]([O:4][C:5]([CH3:7])=[CH2:6])(=[O:3])[CH3:2].[C:8]1([CH3:18])[CH:13]=C[C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC>>[C:1]([O:4][C:5]([C:7]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:18])[CH:13]=1)=[CH2:6])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 14227Trioctylamine

Product 1

HCID 21904108HCID 21904108, compoundYield 60%

Procedure

Using a 15 cm Wiedmer distillation apparatus, a solution of 50 mmol of 3-methyl acetophenone in 15.02 g (150 mmol) of isopropenyl acetate was heated at 95° in the presence of 75 mg of para-toluene sulphonic acid. At a stabilised conversion (50–70% by GC, after 8 h at 95°), the mixture was cooled and 300 mg of trioctylamine were added. After extraction by means of ether, and usual workup, the product was distilled on a bulb-to-bulb apparatus and purified by preparative GC using a 1.2 m×6 mm column loaded with 10% SE-30 on Supelcoport® 80–100 mesh, vector gas: helium at 30 ml/min. The product was obtained in 60% yield

Workup

  1. distillationa 15 cm Wiedmer distillation apparatus
  2. temperatureAt a stabilised conversion (50–70% by GC, after 8 h at 95°), the mixture was cooled
  3. extractionAfter extraction by means of ether, and usual workup
  4. distillationthe product was distilled on a bulb-to-bulb apparatus
  5. custompurified by preparative GC
  6. customThe product was obtained in 60% yield

Sources & evidence

ORD record
ord-42b5c87ab4be468bbf718eb696bec9f4
Source dataset
uspto-grants-2006_10
Patent number
US07129206B2

Reaction notes

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