Methanol → 3-Chloro-2-methylanisole

HRID 354260

Reaction equation

HRID 354260 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.[CH3:13]O>>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([O:10][CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 83682,6-DichlorotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 767493-Chloro-2-methylanisole

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 160° C. for 20 hours, and the pressure rises to about 12 bar. After cooling, the reaction mixture is poured into about 250 ml of water and extracted three times with about 70 ml of dichloromethane. The united organic phases are dried over sodium sulphate and evaporated under reduced pressure. 3-Chloro-2-methylanisole is obtained as an oil (2.5 g, GC analysis: 37.1%, 12% of theory).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with about 70 ml of dichloromethane
  3. dry with materialThe united organic phases are dried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6d8a1a6e004841aeb25f80e049d871d1
Source dataset
uspto-grants-2004_06
Patent number
US06756512B2

Linked notes

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