Water → 3-Chloro-o-cresol

HRID 354259Notes

Reaction equation

HRID 354259 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>CO>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Procedure

8.1 g (0.05 mol) of 2,6-dichlorotoluene and 9.9 g (0.15 mol) of potassium hydroxide (85%) are heated in 40 ml of methanol in an autoclave at 200° C. for 20 hours, which results in a pressure of 30 bar. After cooling, the reaction mixture is poured into 250 ml of water and extracted three times with 70 ml of dichloromethane. The aqueous phase is acidified to pH 1-2 with 30% hydrochloric acid and again extracted three times with 70 ml of dichloromethane each time. The united organic phases are dried over sodium sulphate and evaporated under reduced pressure to give a solid. 3-Chloro-2-methylphenol is obtained as a solid (6.2 g, content by HPLC: 93.5%, 82% of theory).

Workup

  1. customwhich results in a pressure of 30 bar
  2. temperatureAfter cooling
  3. extractionextracted three times with 70 ml of dichloromethane
  4. extractionagain extracted three times with 70 ml of dichloromethane each time
  5. dry with materialThe united organic phases are dried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customto give a solid

Sources & evidence

ORD record
ord-5f01a2769463443bbfa1d45e81416131
Source dataset
uspto-grants-2004_06
Patent number
US06756512B2

Reaction notes

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