3-Chloro-2-methylanisole → 3-Chloro-o-cresol

HRID 354261

Reaction equation

HRID 354261 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([O:8]C)[CH:5]=[CH:6][CH:7]=1>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 767493-Chloro-2-methylanisole

Product 1

HCID 148563-Chloro-o-cresol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3.1 g (0.02 mol) of 3-chloro-2-methylanisole are heated in 20 ml of 50% sulphuric acid for 18 hours with reflux. After cooling, the reaction mixture is extracted three times with dichloromethane, dried over sodium sulphate and concentrated to dryness under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (2.9 g, content by HPLC: 11.7%, 12% of theory).

Workup

  1. temperaturewith reflux
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted three times with dichloromethane
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4f149bc2b5f84728ba42e39fa0b4c854
Source dataset
uspto-grants-2004_06
Patent number
US06756512B2

Linked notes

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