Water → 3-Chloro-o-cresol

HRID 354257

Reaction equation

HRID 354257 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[CH3:9].[OH-:10].[K+].O>C(O)COCCO>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 83682,6-DichlorotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 148563-Chloro-o-cresol

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

16.1 g (0.1 mol) of 2,6-dichlorotoluene and 19.8 g (0.3 mol) of potassium hydroxide (85%) are heated in 30 ml of diethylene glycol at a bath temperature of 190° C. for 18 hours. The water released by the reaction is distilled off. After cooling, the reaction mixture is stirred with 100 ml of water until a solution is obtained and extracted three times with 50 ml of dichloromethane. The aqueous phase is admixed with 35 ml of 30% hydrochloric acid and extracted three times with 70 ml of dichloromethane. The organic phases are dried over sodium sulphate and concentrated under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (12.4 g, content by HPLC: 83%, 72% of theory).

Workup

  1. distillationis distilled off
  2. temperatureAfter cooling
  3. customis obtained
  4. extractionextracted three times with 50 ml of dichloromethane
  5. extractionextracted three times with 70 ml of dichloromethane
  6. dry with materialThe organic phases are dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1b74f2007c514f7bbe541a50993ff04f
Source dataset
uspto-grants-2004_06
Patent number
US06756512B2

Linked notes

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