Water → HCID 11026176, compound

HRID 1870619Notes

Reaction equation

HRID 1870619 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4](F)[C:3]=1[F:14].C(=O)([O-])[O-:16].[K+].[K+].[OH:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:24][CH:23]=1.O>CN1CCCC1=O.C(OCC)(=O)C>[N+:8]([C:7]1[C:6]([F:11])=[C:5]([F:12])[C:4]([O:21][C:22]2[CH:37]=[CH:36][C:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[CH:24][CH:23]=2)=[C:3]([F:14])[C:2]=1[OH:16])([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 7180Benzyl 4-HydroxybenzoateHCID 11430Potassium CarbonateHCID 70154Pentafluoronitrobenzene

Product 1

HCID 11026176HCID 11026176, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
-5 °C

Procedure

42.6 g of pentafluoronitrobenzene (0.2 mol) are dissolved in 300 ml of N-methylpyrrolidone. After 30 g of potassium carbonate (0.22 mol) have been added, the mixture is cooled to -5° C., and a solution of 45.6 g of benzyl 4-hydroxybenzoate (0.2 mol) in 300 ml of N-methylpyrrolidone is then added drop wise over the course of 30 minutes with stirring. After 1 hour, the reaction temperature is raised to 23° C. for 24 hours, and 800 ml of water and 300 ml of ethyl acetate are then added. The organic phase is separated, washed three times with water and dried over sodium sulphate. The solution is then concentrated in a rotary evaporator until yellow crystals precipitate. The reaction product is washed with petroleum ether (boiling range 60-80° C.) collected on a Buchner funnel and dried in a vacuum dryer under nitrogen at 40° C./10 mbar (Yield 89%).

Workup

  1. temperaturethe reaction temperature is raised to 23° C. for 24 hours
  2. customThe organic phase is separated
  3. washwashed three times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationThe solution is then concentrated in a rotary evaporator until yellow crystals precipitate
  6. washThe reaction product is washed with petroleum ether (boiling range 60-80° C.)
  7. customcollected on a Buchner funnel
  8. customdried in a vacuum dryer under nitrogen at 40° C./10 mbar (Yield 89%)

Sources & evidence

ORD record
ord-0b143d88578e4476abfbc38ed3df1bc4
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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