Toluene → Methanone, bis[4-[2-(1-propen-1-yl)phenoxy]phenyl]-

HRID 414147Notes

Reaction equation

HRID 414147 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][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1.[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][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:30][C:27]3[CH:33]=[CH:41][CH:42]=[CH:43][C:44]=3[CH:45]=[CH:40][CH3:46])=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1)=[CH:2][CH3:3]

Participants

6

Reactant 5

HCID 1140TolueneHCID 95824,4'-DifluorobenzophenoneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 156242-Allylphenol

Product 1

HCID 3458330Methanone, bis[4-[2-(1-propen-1-yl)phenoxy]phenyl]-

Conditions

Temperature
100 °C

Procedure

o-Allylphenol (245.6 g), 4,4'-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 between 145°-155° C. and stirred for 31/2 hours. Water and toluene are separated via a Dean Stark trap and finally after 3.5 hours the reaction mixture reaches a temperature of 155° 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 (300 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 4,4'-bis[o-(1-propenyl)phenoxy]benzophenone as a light yellow melt. The yield is 363.3 g.

Workup

  1. customfitted with a stirrer
  2. temperaturereflex condensor and thermometer and the mixture is heated under nitrogen to a temperature between 145°-155° C.
  3. customWater and toluene are separated via a Dean Stark trap and finally after 3.5 hours the reaction mixture
  4. customa temperature of 155° 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 (300 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-664954baaec74303ab8e6b11e3dceb8f
Source dataset
uspto-grants-1988_12
Patent number
US04789704

Reaction notes

Loading…