4-Methoxyphenol → HCID 19078923, compound

HRID 963955Notes

Reaction equation

HRID 963955 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.[C:28]([O-:31])([O-])=O.[K+].[K+].CN(C)[C:36](=[O:38])[CH3:37]>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:38][C:36]4[CH:4]=[CH:3][C:2]([O:31][CH3:28])=[CH:7][CH:37]=4)=[CH:14][CH:13]=3)=[O:11])=[O:9])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 1230724,4'-Difluorobenzil

Product 1

HCID 19078923HCID 19078923, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

To a 200 ml round-bottom flask equipped with a mechanical stirrer, a nitrogen inlet, a thermometer and a Dean-Stark trap fitted with a condenser and a nitrogen outlet were added 4,4'-difluorobenzil (50 mmol, 12.3 g), 4-methoxyphenol (110 mmol, 13.6 g) and anhydrous K2CO3 (70 mmol, 9.7 g). This was followed by the addition of 100 ml N,N-dimethylacetamide (DMAC) and 30 ml toluene as an azeotroping agent. The contents of the flask were maintained at 140°-150° C. for 2-4 h to allow for the complete removal of water from the system. The reaction temperature was further raised to 160° C. and allowed to proceed for a further 12-14 h. The solution was subsequently cooled and filtered. Water was added dropwise to the filtrate with stirring and the precipitate was collected by suction filtration, washed well with water and air dried. The pure product (22 g, 93%) was obtained by recrystallization from isopropyl alcohol. (mp=121°-122° C.).

Workup

  1. customTo a 200 ml round-bottom flask equipped with a mechanical stirrer, a nitrogen inlet
  2. customa thermometer and a Dean-Stark trap fitted with a condenser and a nitrogen outlet
  3. temperatureThe contents of the flask were maintained at 140°-150° C. for 2-4 h
  4. customto allow for the complete removal of water from the system
  5. temperatureThe solution was subsequently cooled
  6. filtrationfiltered
  7. additionWater was added dropwise to the filtrate
  8. filtrationthe precipitate was collected by suction filtration
  9. washwashed well with water and air
  10. customdried

Sources & evidence

ORD record
ord-d08d25a5d41e4d3cbf1e3280a253d4be
Source dataset
uspto-grants-1998_06
Patent number
US05767014

Reaction notes

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