Acetone → HCID 13750614, compound

HRID 1981062Notes

Reaction equation

HRID 1981062 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])=[CH2:2].[CH2:11](Br)[CH:12]=[CH2:13].C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[CH3:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH:12]=[CH2:11])=[CH:6][CH:5]=1)=[CH2:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 584247p-Isopropenylphenol

Product 1

HCID 13750614HCID 13750614, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10 g-portion of p-isopropenylphenol, 1.0 equivalent allyl bromide, 1.0 equivalent K2CO3, and 20 ml acetone were mixed and refluxed overnight. The reaction mixture was poured into 60 ml water and extracted with two portions of ether. The combined ether layers were washed with two portions of 10% aqueous NaOH, two portions of saturated aqueous NaCl and dried over K2CO3. Removal of solvent followed by distillation under reduced pressure gave a 63% yield of 1-(1-methylethenyl)-4-(2-propenyloxy)benzene, mp 22°-23° C.

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted with two portions of ether
  3. washThe combined ether layers were washed with two portions of 10% aqueous NaOH, two portions of saturated aqueous NaCl
  4. dry with materialdried over K2CO3
  5. customRemoval of solvent
  6. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-fc17efa045af4c838e3361da586619b5
Source dataset
uspto-grants-1985_04
Patent number
US04511731

Reaction notes

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