Chlorodifluoromethane → [4-(difluoromethoxy)phenyl](phenyl)methanone

HRID 2107530Notes

Reaction equation

HRID 2107530 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[F:18][CH:19]([F:21])Cl>O.O1CCOCC1>[F:18][CH:19]([F:21])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 143474-HydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 3315228[4-(difluoromethoxy)phenyl](phenyl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

100 g of 4-hydroxybenzophenone and 200 g of sodium hydroxide are dissolved in a mixture of 1 l of water and 500 ml of dioxane. The mixture is heated to 70° C. and a vigorous stream of difluorochloromethane (Frigen 22) is introduced. After 2 hours, the mixture is cooled to room temperature and 1 l of water is added to the contents of the flask. The mixture is extracted three times using 1.2 l of chloroform each time, the chloroform phase is extracted by shaking with 1N sodium hydroxide solution, washed with water and the organic phase is dried using potassium carbonate. After stripping off the solvent and subsequent distillation under vacuum, 60 g (48%) of 4-difluoromethoxybenzophenone are obtained as a pale yellow oil.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. extractionThe mixture is extracted three times
  3. extractionthe chloroform phase is extracted
  4. washwashed with water
  5. customthe organic phase is dried
  6. distillationthe solvent and subsequent distillation under vacuum, 60 g (48%) of 4-difluoromethoxybenzophenone
  7. customare obtained as a pale yellow oil

Sources & evidence

ORD record
ord-5586fcad8c2941bbb73dae7b93a7a6dc
Source dataset
uspto-grants-1990_06
Patent number
US04935414

Reaction notes

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