Perfluoro propyl vinyl ether → Dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate

HRID 336069Notes

Reaction equation

HRID 336069 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:16]([F:31])([O:20][C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])=[C:17]([F:19])[F:18]>C(=O)([O-])[O-].[K+].[K+].C1COCC1>[F:19][C:17]([F:18])([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:16]([F:31])[O:20][C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26]

Participants

5

Reactant 2

HCID 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)isophthalateYield 85.12%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
66 °C

Procedure

In a nitrogen purged dry box, THF (500 mL) and dimethyl 5-hydroxy-isophthalate (42 g, 0.20 mol) were added to an oven-dried round bottom reaction flask equipped with a stirrer and addition funnel. Potassium carbonate catalyst (6.955 g, 0.0504 mol) was added via the addition funnel to form a reaction mixture. Subsequently PPVE (79.8 g, 0.30 mol) was added via the addition funnel and the thus formed reaction mixture was heated to reflux at 66° C. for 16 hours. The catalyst was then removed from the resulting mixture via filtration through a bed of silica gel. The filtrate thus produced was concentrated under vacuum using a rotary evaporator, followed by vacuum distillation to give 81.04 g (85.12% yield) of the desired dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate (F10-iso) collected as the distillate.

Workup

  1. customIn a nitrogen purged
  2. customdry box
  3. customequipped with a stirrer and addition funnel
  4. customto form a reaction mixture
  5. customthe thus formed reaction mixture
  6. temperaturewas heated
  7. customThe catalyst was then removed from the resulting mixture via filtration through a bed of silica gel
  8. customThe filtrate thus produced
  9. concentrationwas concentrated under vacuum
  10. customa rotary evaporator
  11. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-1f1f469b4d644327b6c1cc920e647670
Source dataset
uspto-grants-2014_11
Patent number
US08889256B2

Reaction notes

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