Sulfuric Acid → 5,5,5-Trifluoro-4-(trifluoromethyl)penta-1,3-diene

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]([C:9]([F:12])([F:11])[F:10])(O)[CH2:4][CH:5]=[CH:6]C.OS(O)(=O)=O>>[F:1][C:2]([F:13])([F:14])[C:3]([C:9]([F:10])([F:11])[F:12])=[CH:4][CH:5]=[CH2:6]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 86613238HCID 86613238, compound

Product 1

HCID 232352135,5,5-Trifluoro-4-(trifluoromethyl)penta-1,3-dieneYield 45.5%

Conditions

Temperature: 95 °C

Procedure

The crude 1,1-bis(trifluoromethyl)-3-penten-1-ol (54 grams) can be placed in a 250 mL three-neck flask and 125 mL of concentrate H2SO4 added to form a mixture which can be stirred and heated slowly to 95° C. (separating compounds having lower boiling points from the mixture between 34° C. and 55° C.). The 1,1,1-trifluoro-2-trifluoromethyl-2,4-pentadiene (15.6 grams, 45.5% yield) produced can be separate from the mixture as a gas between 70° C. and 74° C.

Workup

customseparating compounds
customfrom the mixture between 34° C. and 55° C.

Sources & evidence

ORD record: ord-216330130d8b462f90ea0dc8f0551526
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318656B2

Reaction notes

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