Acetone → 13990-72-2

HRID 1730202Notes

Reaction equation

HRID 1730202 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[CH:10]=[CH2:11].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:10]=[CH2:9]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 63734213990-72-2

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 336.3 parts of 4-fluorophenol, 417.5 parts of allyl bromide, 420 parts of potassium carbonate and 480 parts of acetone is stirred and refluxed for 8 hours. After cooling to room temperature, 2250 parts of water are added. The aqueous layer is separated and extracted twice with ether. The combined extracts are washed successively twice with sodium hydroxide solution 10% and twice with sodium chloride solution, dried over potassium carbonate, filtered and evaporated. The oil residue is distilled in vacuo, yielding 381.8 parts of 4-allyloxy-fluorobenzene; bp. 93° C at 23 mm. pressure; nD20 : 1.4950;d2020 : 1.070.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe aqueous layer is separated
  3. extractionextracted twice with ether
  4. washThe combined extracts are washed successively twice with sodium hydroxide solution 10% and twice with sodium chloride solution
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe oil residue is distilled in vacuo

Sources & evidence

ORD record
ord-32abde345f2d4b4a99ab3343ae102ad0
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

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