M-Cresol → 1-(Difluoromethoxy)-3-methylbenzene

HRID 1762406Notes

Reaction equation

HRID 1762406 reaction equation
Cl[CH:2]([F:4])[F:3].[CH:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12].[OH-].[Na+].O1CCOCC1>O>[F:3][CH:2]([O:11][C:10]1[CH:5]=[C:6]([CH3:12])[CH:7]=[CH:8][CH:9]=1)[F:4]

Participants

6

Reactant 4

HCID 342M-CresolHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 312751,4-Dioxane

Product 1

HCID 144612951-(Difluoromethoxy)-3-methylbenzeneYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
68 °C

Procedure

260 parts by weight of chlorodifluoromethane are passed over 10 hours, whilst stirring, into a mixture of 221 parts by weight of m-cresol, 412 parts by weight of sodium hydroxide, 600 parts by volume of 1,4-dioxane and 500 parts by volume of water, at 67°-70° C. After stirring for 45 minutes at 68° C., the reaction mixture is cooled, diluted with 1,000 parts by volume of water and extracted four times with 200 parts by volume of diethyl ether. After drying, concentrating under reduced pressure and distilling, 209 parts by weight (yield: 64.5% of theory) of 3-tolyl difluoromethyl ether of boiling point 64°-67° C./24.7 mbar are obtained.

Workup

  1. temperaturethe reaction mixture is cooled
  2. extractionextracted four times with 200 parts by volume of diethyl ether
  3. customAfter drying
  4. concentrationconcentrating under reduced pressure
  5. distillationdistilling

Sources & evidence

ORD record
ord-a4b9ff5f0eec461c81b6103be9453140
Source dataset
uspto-grants-1989_05
Patent number
US04832879

Reaction notes

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