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Hydrochloric Acid → 4-(Trifluoromethyl)-4,5,5,5-tetrafluoropent-1-ene

HRID 1879610
Notes
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Reaction equation

HRID 1879610 reaction equation
[F:1][C:2]([C:12]([F:15])([F:14])[F:13])([C:8]([F:11])([F:10])[F:9])[CH2:3][CH:4](I)[CH2:5]O.Cl>[Zn].C(O)(=O)C>[F:1][C:2]([C:12]([F:13])([F:14])[F:15])([C:8]([F:9])([F:10])[F:11])[CH2:3][CH:4]=[CH2:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27826014,5,5,5-Tetrafluoro-2-iodo-4-(trifluoromethyl)pentan-1-ol

Product 1

HCID 202612974-(Trifluoromethyl)-4,5,5,5-tetrafluoropent-1-ene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

About 11 g of the RF-intermediate 4,5,5,5-tetra fluoro-4-(trifluoromethyl)-2-iodopentan-1-ol can be added to a glass pressure tube and about 13 grams of 30% (wt/wt) aqueous acetic acid can be added to the other tube to form a mixture. The mixture can be heated to about 80° C., and 4 grams of powdered zinc can be added slowly through a solid addition system. The mixture can be allowed to stir for an additional 2 hours before being cooled and adding 2 mL of 1.5 N HCl to phase separate the mixture. The organic layer can be decanted to give 3 grains of the RF-intermediate 4,5,5,5-tetrafluoro-4-(trifluoromethyl)pentan-1-ene which can be 75.14% (area percent by gas chromatography).

Workup

  1. temperaturebefore being cooled
  2. customseparate the mixture
  3. customThe organic layer can be decanted

Sources & evidence

ORD record
ord-c23a72de4c2c49789f490521db1f9ab2
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318656B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes