Toluene → HCID 53941966, compound

HRID 414148Notes

Reaction equation

HRID 414148 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH:2]=[CH2:3].F[C:12]1[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=1)=[O:15].[C:27](=[O:30])([O-])[O-].[K+].[K+].[CH3:33]N1CCCC1=O.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:12]1[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:30][C:27]2[CH:33]=[CH:41][CH:42]=[CH:43][C:44]=2[CH:45]=[CH:40][CH3:46])=[CH:18][CH:17]=1)=[O:15])=[CH:2][CH3:3]

Participants

6

Reactant 5

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 156242-AllylphenolHCID 676512,4'-Difluorobenzophenone

Product 1

HCID 53941966HCID 53941966, compound

Conditions

Temperature
160 °C

Procedure

o-Allylphenol (245.6 g), 2,4'-difluorobenzophenone (200 g), potassium carbonate (187.4 g), dry N-methylpyrrolidone (700 ml) and toluene (250 ml) are placed in a 3-necked 2500 ml flask fitted with a stirrer, reflex condensor and thermometer and the mixture is heated under nitrogen to a temperature of 160° C. and stirred for 8 hours. Water and toluene are separated via a Dean Stark trap and finally after 8 hours the reaction mixture reaches a temperature of 160° C. The mixture is cooled to 100° C. and a 1:1 mixture of toluene/water (1100 ml) is added while stirring. After phase separation the aqueous layer is washed with toluene (200 ml) and the combined toluene layers are washed 4 times with water (400 ml). The toluene phase is dried over sodium sulphate and toluene distilled off by use of a rotary evaporator finally in vacuum leaving 2,4'-bis[o-(1-propenyl)phenoxy]benzophenone as a light yellow melt. The yield is 396 g.

Workup

  1. customfitted with a stirrer
  2. customWater and toluene are separated via a Dean Stark trap and finally after 8 hours the reaction mixture
  3. customa temperature of 160° C
  4. temperatureThe mixture is cooled to 100° C.
  5. additiona 1:1 mixture of toluene/water (1100 ml)
  6. additionis added
  7. stirringwhile stirring
  8. customAfter phase separation the aqueous layer
  9. washis washed with toluene (200 ml)
  10. washthe combined toluene layers are washed 4 times with water (400 ml)
  11. dry with materialThe toluene phase is dried over sodium sulphate and toluene
  12. distillationdistilled off by use of a rotary evaporator finally in vacuum

Sources & evidence

ORD record
ord-33076931cb93419a8744faa1b6f48ab2
Source dataset
uspto-grants-1988_12
Patent number
US04789704

Reaction notes

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