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

HRID 2049821Notes

Reaction equation

HRID 2049821 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][C:13]([CH3:15])=[CH2:14]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][C:13]([CH3:15])=[CH2:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 112413-Chloro-2-methyl-1-propene2×HCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4chlorophenol (10 g, 0.78 mol) and sodium hydride (1.9 g, 0.08 mol) is heated to reflux for 30 min in 30 ml of THF and then cooled. 3-Chloro-2-methyl-1-propene (7.3 g, 0.08 mol) in 10 ml THF is added and the mixture is heated to reflux. After 24 hr, an additional equivalent of 3-chloro-2-methyl-1-propene is added and the mixture heated under reflux for another 24 hr. The reaction mixture is cooled and diluted with ether to 150 ml, washed with 20% NaOH (2X) and with water until neutral, then dried and solvent is removed to yield 3-(4-chloro-phenoxy)-2-methyl-1-propene.

Workup

  1. temperatureis heated
  2. temperaturecooled
  3. temperaturethe mixture is heated to reflux
  4. temperaturethe mixture heated
  5. temperatureunder reflux for another 24 hr
  6. temperatureThe reaction mixture is cooled
  7. washwashed with 20% NaOH (2X) and with water until neutral,
  8. customthen dried
  9. customsolvent is removed

Sources & evidence

ORD record
ord-2ff02eea9a7a4e3b9b78a521fbd3bf3d
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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