Allyl bromide → HCID 13066667, compound

HRID 1164064Notes

Reaction equation

HRID 1164064 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[CH2:18]([C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[Cl:1])[CH:10]=[CH:9][C:8]=1[OH:11])[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 5121102HCID 5121102, compound

Product 1

HCID 13066667HCID 13066667, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
230 °C

Procedure

A mixture of 4-(2-chlorophenoxy)phenol (15 g), allyl bromide (12.5 g) and potassium carbonate (14 g) in methyl isobutyl ketone (100 ml) was refluxed under heating for 3 hours. After cooling, the reaction mixture was filtered, and the filtrate was evaporated. The residue was dissolved in diethyl ether, washed with dil. aqueous sodium hydroxide and water, dried and evaporated. The oily residue was stirred in a oil bath at 230° C. for 2 hours and distilled to give 2-allyl-4-(2-chlorophenoxy)phenol (14.7 g). bp 189°-192° C./3 mmHg.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washwashed with dil. aqueous sodium hydroxide and water
  8. customdried
  9. customevaporated
  10. distillationdistilled

Sources & evidence

ORD record
ord-c43fe311f8bd494c9f86f5d0b50de939
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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