Hydrochloric Acid → HCID 58419187, compound

HRID 1803724Notes

Reaction equation

HRID 1803724 reaction equation
[F:1][C:2]([F:41])([O:26][C:27]1[CH:36]=[C:35]([C:37]([O:39]C)=[O:38])[CH:34]=[CH:33][C:28]=1[C:29]([O:31]C)=[O:30])[CH:3]([F:25])[O:4][C:5]([F:24])([F:23])[C:6]([F:22])([O:11][C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[C:7]([F:10])([F:9])[F:8].[OH-].[K+].Cl>O>[F:1][C:2]([F:41])([O:26][C:27]1[CH:36]=[C:35]([C:37]([OH:39])=[O:38])[CH:34]=[CH:33][C:28]=1[C:29]([OH:31])=[O:30])[CH:3]([F:25])[O:4][C:5]([F:23])([F:24])[C:6]([F:22])([O:11][C:12]([F:20])([F:21])[C:13]([F:18])([F:19])[C:14]([F:16])([F:15])[F:17])[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58419191HCID 58419191, compound

Product 1

HCID 58419187HCID 58419187, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Dimethyl 2-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)-propoxy)ethoxy)terephthalate as prepared in Example 11 (2.25 g, 0.035 mol) was added to a solution of water (50 mL) and potassium hydroxide (KOH, 1.96 g) in a reaction flask. The resulting solution in the reaction flask was heated for 5 hours, cooled to room temperature (about 25° C.) and then acidified by adding concentrated HCl to the reaction flask until a pH of ˜1 was achieved, determined by the formation of a precipitate in the reaction flask. The resulting precipitate was filtered and dried under vacuum. Proton NMR of this precipitate showed the desired material, 2-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)terephthalic acid. The precipitate was then crystallized from ethyl acetate (EtOAc, ˜1 part) and hexane (˜4 parts). After filtration and drying under vacuum, the resulting white di-acid, 2-(1,1,2-trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)ethoxy)terephthalic acid, had a melting point of 236-239° C.

Workup

  1. temperatureThe resulting solution in the reaction flask was heated for 5 hours
  2. filtrationThe resulting precipitate was filtered
  3. customdried under vacuum
  4. customThe precipitate was then crystallized from ethyl acetate (EtOAc, ˜1 part) and hexane (˜4 parts)
  5. filtrationAfter filtration
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-f37a82a3a40f44dbb243e78454d202ab
Source dataset
uspto-grants-2013_01
Patent number
US08350099B2

Reaction notes

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