Allyl bromide → Benzene, 1,2-dichloro-3-(2-propenyloxy)-

HRID 371731

Reaction equation

HRID 371731 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 113342,3-DichlorophenolHCID 11430Potassium Carbonate

Product 1

HCID 637359Benzene, 1,2-dichloro-3-(2-propenyloxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-dichlorophenol (35.5 g., 0.22 mole), allyl bromide (29.4 g., 0.24 mole) and potassium carbonate (33 g., 0.24 mole) in dimethylformamide (200 ml.) is vigorously stirred and heated at 55°-60° C. for 1 hour, poured into ice water, extracted with ether, washed with water and dried over magnesium sulfate. Evaporation of the ether leaves 2,3-dichlorophenyl allyl ether which is subjected to a Claisen rearrangement by heating at 250° C. for 10 minutes. Distillation gives 36 g. of 2,3-dichloro-6-allylphenol which boils at 132°-134°/13 mm.

Workup

  1. temperatureheated at 55°-60° C. for 1 hour
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the ether

Sources & evidence

ORD record
ord-0243c53bdbd44dd79d87bf6981e94229
Source dataset
uspto-grants-1978_05
Patent number
US04087542

Linked notes

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