Toluene → HCID 12080910, compound

HRID 498160Notes

Reaction equation

HRID 498160 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 962WaterSolvent2×

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, 60 ml of N,N-dimethylformamide and 190 ml of toluene were placed. The resultant mixture was stirred at 165° C. for 4 hours while water formed as the byproduct was removed by azeotropic distillation. After cooling, the obtained reaction mixture was poured into 3 liters of ion-exchanged water and the product was precipitated. The formed precipitates were separated by filtration and washed with ion-exchanged water and ethanol. The obtained light yellow solid substance was dried under a reduced pressure at 50° C. for 1 day and 142.01 g of a product was obtained (the yield: 68%).

Workup

  1. customInto a 2 liter four-necked flask equipped with a thermometer, a stirrer
  2. customformed as the byproduct
  3. customwas removed by azeotropic distillation
  4. temperatureAfter cooling
  5. customthe obtained reaction mixture
  6. customthe product was precipitated
  7. customThe formed precipitates
  8. customwere separated by filtration
  9. washwashed with ion-exchanged water and ethanol
  10. customThe obtained light yellow solid substance was dried under a reduced pressure at 50° C. for 1 day

Sources & evidence

ORD record
ord-5e89c4abf1c24f8a9cbf96492c7bbfb3
Source dataset
uspto-grants-2005_09
Patent number
US06949674B2

Reaction notes

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