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Tributylamine → 3,3,3-Trifluoro-2-(trifluoromethyl)-1-propene

HRID 35390
Notes
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Reaction equation

HRID 35390 reaction equation
C(N(CCCC)CCCC)CCC.[F:14][C:15]([F:27])([F:26])[CH:16]([C:22]([F:25])([F:24])[F:23])[C:17](OCCl)=O>>[F:14][C:15]([F:27])([F:26])[C:16]([C:22]([F:25])([F:24])[F:23])=[CH2:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 7622TributylamineHCID 13954659Monochloromethyl 2-trifluoromethyl-3,3,3-trifluoropropanoate

Product 1

HCID 914503,3,3-Trifluoro-2-(trifluoromethyl)-1-propeneYield 75.9%

Conditions

Temperature
65 °C

Procedure

In a four necked 100 ml flask equipped with a condenser, a dropping funnel and a thermometer, tributylamine (20.0 g, 108 mmoles) was charged and warmed to 65° C. Monochloromethyl 2-trifluoromethyl-3,3,3-trifluoropropanoate (4.88 g, 20 mmol) was dropwise added thereto while stirring. The reaction was continued at the same temperature as above for 3 hours while stirring. The gas evolved from a top of the condenser was washed with an alkaline solution, dried with alumina and cooled. The resultant liquid was distilled to give 2-trifluoromethyl-3,3,3-trifluoropropene (2.49 g). Yield, 76 %.

Workup

  1. customIn a four necked 100 ml flask equipped with a condenser, a dropping funnel
  2. customwas continued at the same temperature as above for 3 hours
  3. stirringwhile stirring
  4. washwas washed with an alkaline solution
  5. customdried with alumina
  6. temperaturecooled
  7. distillationThe resultant liquid was distilled

Sources & evidence

ORD record
ord-d57e115760924d43a21fc3df3125c5f3
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766238

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes