Phenol → HCID 57057502, compound

HRID 1493431Notes

Reaction equation

HRID 1493431 reaction equation
C(OC1C=CC=CC=1)=CC.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.C1(O)C=CC=CC=1.[CH2:28]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1/[CH:38]=[CH:39]/[CH3:40])[CH:29]=[CH2:30]>CC(C)=O>[CH2:28]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]=[CH:39][CH3:40])[CH:29]=[CH2:30]

Participants

7

Reactant 5

HCID 996PhenolHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 3533755HCID 3533755, compoundHCID 11171268HCID 11171268, compound

Product 1

HCID 57057502HCID 57057502, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

O-propenylphenol (67 g) was added to a stirred suspension of potassium carbonate (138 g) in dry acetone. Allyl bromide (67 g) was then added dropwise over about 20 minutes and the stirred mixture was heated under reflux for 4 hours. After this time, gas liquid chromatography indicated that the phenol had been converted to about 95% of a mixture of cis and trans 2-allyloxy-1-propenylbenzene. The mixture was filtered and the solvent removed under reduced pressure. The residue was vacuum distilled and yielded 58.9 g of almost pure 2-allyloxy-1-propenylbenzene which was identified spectroscopically. [b.p. 64-88° C. at 0.6 mbar].

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe mixture was filtered
  4. customthe solvent removed under reduced pressure
  5. distillationdistilled

Sources & evidence

ORD record
ord-3de632b9268c44fa87b847a46594feba
Source dataset
uspto-grants-1991_06
Patent number
US05021512

Reaction notes

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