4-Chlorophenol → 3-(4-Chlorophenoxy)2-methyl-1-propene

HRID 2049816Notes

Reaction equation

HRID 2049816 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+].Cl[CH2:16][C:17]([CH3:19])=[CH2:18].C(OCC)(=O)C.CCCCCC>CN(C=O)C.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:17]([CH3:19])=[CH2:16])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 112413-Chloro-2-methyl-1-propene2×HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 124099273-(4-Chlorophenoxy)2-methyl-1-propene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-chlorophenol (10 g, 0.078 mol) and potassium carbonate (32.25 g, 0.233 mol) in 20 ml DMF is stirred for 30 min at 25°. 1.1 Equivalents of 3-chloro-2-methyl-1-propene in 10 ml DMF is added dropwise at 0° and the mixture is allowed to warm to RT. After stirring at RT for 19 hr, the reaction is checked by thin layer chromatography (TLC) developing with 30% ethyl acetate/hexane. As some starting alcohol is still present, another 0.5 equivalent of 3-chloro-2-methyl-1-propene is added (a total of 1.6 equivalents) and the reaction mixture is heated at 50° for 7 hr. The reaction product is worked up with ice water and ether. The organic phase is washed with 5% NaOH, water until neutral, brine, and dried over magnesium sulfate and solvent is removed to give 3-(4-chlorophenoxy)-2-methyl-1-propene.

Workup

  1. stirringAfter stirring at RT for 19 hr
  2. temperatureis heated at 50° for 7 hr
  3. washThe organic phase is washed with 5% NaOH, water until neutral, brine
  4. dry with materialdried over magnesium sulfate and solvent
  5. customis removed

Sources & evidence

ORD record
ord-45ddc0342b5243f5abdc0599b0088023
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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