Acetone → p-Prenylacetophenone

HRID 1413829Notes

Reaction equation

HRID 1413829 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:9][CH:8]=2)OCC[O:3]1.Cl.CC(C)=O.C(=O)([O-])O.[Na+]>O>[CH2:13]([C:10]1[CH:9]=[CH:8][C:7]([C:2](=[O:3])[CH3:1])=[CH:12][CH:11]=1)[CH:14]=[C:15]([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 204676122-Methyl-2-(p-prenylphenyl)-1,3-dioxolane

Product 1

HCID 11217703p-PrenylacetophenoneYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 69.0 g of 2-methyl-2-(p-prenylphenyl)-1,3-dioxolane, 8 ml of 6 N hydrochloric acid and 400 ml of acetone was stirred at room temperature for 3 hours. A solution of 5.0 g of sodium hydrogen carbonate and 200 ml of water was added to the solution, which was extracted with ethyl ether after removal of the acetone. The ethereal solution was washed with water, dried, concentrated and distilled to give 54.6 g of p-prenylacetophenone, b.p. 110-112 °C/0.05 mmHg.

Workup

  1. extractionwas extracted with ethyl ether
  2. customafter removal of the acetone
  3. washThe ethereal solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-a9fd5e64dd0b45859c5e987ee649d3af
Source dataset
uspto-grants-1981_02
Patent number
US04251543

Reaction notes

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