4-Chlorophenol → p-Chlorophenyl allyl ether

HRID 2164895Notes

Reaction equation

HRID 2164895 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)(OC)O[CH2:11][CH:12]=[CH2:13]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH:12]=[CH2:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 46844-ChlorophenolHCID 534788Methyl 2-propen-1-yl carbonate

Product 1

HCID 257946p-Chlorophenyl allyl etherYield 97.3%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chlorophenol (1.28 g, 10 mmoles), allyl methyl carbonate (1.40 g, 12 mmoles), palladium acetate (11 mg, 0.05 mmole) and triphenyl phosphine (40 mg, 0.15 mmole) is heated at 70° C. for 2.5 hours. After removal of volatiles, the residue is subjected to bulb-to-bulb distillation (110° C., 4 mm Hg) to give 1.64 g, 97 percent of allyl 4-chlorophenyl ether.

Workup

  1. customAfter removal of volatiles
  2. distillationthe residue is subjected to bulb-to-bulb distillation (110° C., 4 mm Hg)

Sources & evidence

ORD record
ord-5db639bf8914462ab9e8c2ae1c805648
Source dataset
uspto-grants-1985_03
Patent number
US04507492

Reaction notes

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