Toluene → HCID 12080910, compound

HRID 2195581Notes

Reaction equation

HRID 2195581 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.CN(C)C=O.C1(C)C=CC=CC=1>O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([O:1][C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 12080910HCID 12080910, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 2 liter four-necked flask equipped with a thermometer, a stirrer and a Dean-Stark distillation apparatus, 133.24 g (0.63 moles) of dimethyl 5-hydroxyisophthalate, 107.33 g (0.76 moles) of 4-fluoronitrobenzene, 760 ml of N,N-dimethylformamide and 190 ml of toluene were placed, and the resultant mixture was stirred at 165° C. for 4 hours while water formed by the reaction was removed as an azeotrope with toluene. After the reaction fluid was cooled, the reaction fluid was added into 3 liters of ion-exchanged water, and the product was precipitated. The precipitated product was separated by filtration and washed with ion-exchanged water and ethanol. The obtained light yellow solid substance was dried at 50° C. for 1 day under a reduced pressure, and 142.01 g of the first intermediate compound was obtained (the yield: 68%).

Workup

  1. customInto a 2 liter four-necked flask equipped with a thermometer, a stirrer
  2. customformed by the reaction
  3. customwas removed as an azeotrope with toluene
  4. temperatureAfter the reaction fluid was cooled
  5. additionthe reaction fluid was added into 3 liters of ion-exchanged water
  6. customthe product was precipitated
  7. customThe precipitated product was separated by filtration
  8. washwashed with ion-exchanged water and ethanol
  9. customThe obtained light yellow solid substance was dried at 50° C. for 1 day under a reduced pressure

Sources & evidence

ORD record
ord-1a2d711b9d7949288adc8395fbb3ac7f
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

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