Acetone → 13990-72-2

HRID 328627Notes

Reaction equation

HRID 328627 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 oily 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 oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-647e4a60349f4ef8aa0150ae4f015196
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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