2,5-Dichlorophenol → 2,5-Dichloroanisole

HRID 568625Notes

Reaction equation

HRID 568625 reaction equation
COS([O:6][CH3:7])(=O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1O.[OH-].[Na+]>O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 662,5-DichlorophenolHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide

Product 1

HCID 161252,5-Dichloroanisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylsulfate (94.64 g) is added dropwise over a 40 minute period to a cooled stirred solution of 2,5-dichlorophenol (122.25 g) and sodium hydroxide (31.5 g) in water (300 ml). This mixture is stirred at room temperature for one hour then at reflux for 2 hours, then cooled to room temperature. The organic layer is separated and combined with ether extracts of the remaining aqueous layer. The ether solution is dried (saturated NaCl, Na2SO4, K2CO3) and the ether removed to give 2,5-dichloroanisole. Distillation gives a colorless liquid (115° C. at aspirator vacuum).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled to room temperature
  3. customThe organic layer is separated
  4. dry with materialThe ether solution is dried (saturated NaCl, Na2SO4, K2CO3)
  5. customthe ether removed

Sources & evidence

ORD record
ord-b4401701b8534f7b834d2c67dacfdff2
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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