Potassium Carbonate → Dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate

HRID 2366504Notes

Reaction equation

HRID 2366504 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].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]([F:37])([F:36])[C:24]([F:35])([F:34])[C:25]([F:33])([F:32])[O:26][C:27]([F:31])=[C:28]([F:30])[F:29]>C1COCC1>[F:30][C:28]([F:29])([O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[CH:27]([F:31])[O:26][C:25]([F:32])([F:33])[C:24]([F:34])([F:35])[C:23]([F:22])([F:36])[F:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15388Perfluoro propyl vinyl etherHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 58426160Dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (12 liters) and dimethyl 5-hydroxy-isophthalate (2100 g) were combined under nitrogen in an oil jacketed 22 liter RB flask equipped with a condenser, mechanical stirrer, pressure equalizing addition funnel. To this stirred solution was added anhydrous potassium carbonate (1035 g), followed by 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluorovinyloxy)propane (3192 g). Ca. 2 liters of additional THF was used to wash all the reagents into the reaction vessel. The resulting mixture was refluxed for 10.5 hours.

Workup

  1. customequipped with a condenser, mechanical stirrer
  2. additionaddition funnel
  3. washto wash all the reagents into the reaction vessel
  4. temperatureThe resulting mixture was refluxed for 10.5 hours

Sources & evidence

ORD record
ord-89c4f26c03744f2cb7e315077707abcd
Source dataset
uspto-grants-2014_04
Patent number
US08697816B2

Reaction notes

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