4-Chlorophenol → p-Chlorophenyl allyl ether

HRID 1772223Notes

Reaction equation

HRID 1772223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH:16]=[CH2:17]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:16]=[CH2:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 257946p-Chlorophenyl allyl etherYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chlorophenol (30 g, 233 mmol) in acetonitrile (100 ml) was added potassium carbonate (48.1 g, 349 mmol, 1.5 eq) and allyl bromide (36.28 g, 299.9 mmol, 1.3 eq) dropwise with stirring for 5 hours at 50° C. in an oil bath. The solids were filtered out and the liquid was concentrated under vacuum to afford 1-chloro-4-(prop-2-en-1-yloxy)benzene as yellow oil (34 g, 86%); 1H NMR (300 MHz, CDCl3): δ 7.20-7.25 (m, 2H), 6.81-6.86 (m, 2H), 5.96-6.09 (m, 1H), 5.27-5.44 (m, 2H), 4.49-4.51 (m, 2H).

Workup

  1. filtrationThe solids were filtered out
  2. concentrationthe liquid was concentrated under vacuum

Sources & evidence

ORD record
ord-a1ecb07c22b24086b58efabbe08cdb43
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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