1,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester → Dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate

HRID 1803723Notes

Reaction equation

HRID 1803723 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].CC(C)([O-])C.[K+].[F:22][C:23]([F:47])([F:46])[C:24]([F:45])([F:44])[C:25]([F:43])([F:42])[O:26][C:27]([F:41])([C:32]([F:40])([F:39])[O:33][C:34]([F:38])=[C:35]([F:37])[F:36])[C:28]([F:31])([F:30])[F:29]>O1CCCC1>[F:37][C:35]([F:36])([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:34]([F:38])[O:33][C:32]([F:39])([F:40])[C:27]([F:41])([O:26][C:25]([F:42])([F:43])[C:24]([F:44])([F:45])[C:23]([F:22])([F:46])[F:47])[C:28]([F:31])([F:30])[F:29]

Participants

5

Reactant 3

HCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 1026621,1,1,2,3,3-Hexafluoro-2-(heptafluoropropoxy)-3-((trifluorovinyl)oxy)propaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 58419190Dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dry box, tetrahydrofuran (THF, 1000 mL) and dimethyl 5-hydroxyisophthalate (42.00 g, 0.20 mol) were added to an oven dry round bottom reaction flask equipped with a stirrer to form a reaction mixture. Potassium t-butoxide (6.16 g, 0.055 mol) was added to the reaction flask. 1,1,1,2,2,3,3-Heptafluoro-3-(1,1,1,2,3,3-hexafluoro-3-(1,2,2trifluorovinyloxy)propan-2-yloxy)propane (216 g, 0.50 mol) was then added via the addition funnel to the reaction mixture, and the reaction allowed to stir at room temperature. After 24 hour the reaction was terminated via the addition of 80 mL of 10% HCl. The reaction mixture was concentrated at reduced pressure, diluted with dichloromethane, washed with 10% HCl (2×100 mL) and then with water (2×100 mL), to form an aqueous phase and an organic phase. The separated organic phase was dried over anhydrous sodium sulfate and was then concentrated at reduced pressure to form a crude product. The crude product was purified by column chromatography to give 86.07 g (67.32%) yield of the desired material, dimethyl 5-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)isophthalate.

Workup

  1. customdry round bottom reaction flask
  2. customequipped with a stirrer
  3. customto form a reaction mixture
  4. customAfter 24 hour the reaction was terminated via the addition of 80 mL of 10% HCl
  5. concentrationThe reaction mixture was concentrated at reduced pressure
  6. additiondiluted with dichloromethane
  7. washwashed with 10% HCl (2×100 mL)
  8. customwith water (2×100 mL), to form an aqueous phase
  9. dry with materialThe separated organic phase was dried over anhydrous sodium sulfate
  10. concentrationwas then concentrated at reduced pressure
  11. customto form a crude product
  12. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b1b10f45a26945989374c8b353905649
Source dataset
uspto-grants-2013_01
Patent number
US08350099B2

Reaction notes

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