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Water → 2,2,2-Trifluoroethyl Acetate

HRID 420420
Notes
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Reaction equation

HRID 420420 reaction equation
[CH2:1]([OH:6])[C:2]([F:5])([F:4])[F:3].C(N(CC)CC)C.[C:14](Cl)(=[O:16])[CH3:15].O>C(OCC)C>[C:14]([O:6][CH2:1][C:2]([F:5])([F:4])[F:3])(=[O:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 64092,2,2-TrifluoroethanolHCID 8471Triethylamine

Product 1

HCID 1362562,2,2-Trifluoroethyl AcetateYield 72.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

85 g (0.85 mol) of trifluoroethanol and 80 ml of diethyl ether were poured to a four-neck flask of 2 liter, and further 129 g (1.27 mmol/1.49 eq) of triethylamine was added thereto. Then, the resultant mixture was ice-cooled and stirred while dropping a solution diluting 100 g (1.27 mol/1.49 eq) of acetyl chloride with 80 ml of diethyl ether by dropping funnel. While dropping, the temperature of the resultant reacted solution was kept between 27 to 35° C. The period of time for dropping was 20 minutes. After that, the resultant mixed solution was stirred for 1.5 hours at room temperature and 350 ml of water was added, then, the reaction was completed. Subsequently, an organic phase was separated by the separatory funnel and dried using magnesium sulfate. Thereafter, purification by distilling was conducted to obtain 88 g of 2,2,2-trifluoroethyl acetate (CH3COOCH2CF3) of which yield was 72.9%.

Workup

  1. additionwas added
  2. temperaturecooled
  3. customthe temperature of the resultant reacted solution
  4. customwas kept between 27 to 35° C
  5. additionAfter that, the resultant mixed solution
  6. stirringwas stirred for 1.5 hours at room temperature
  7. customSubsequently, an organic phase was separated by the separatory funnel
  8. customdried
  9. customThereafter, purification
  10. distillationby distilling

Sources & evidence

ORD record
ord-8f312fc7dd90401daed4df06ef8cc951
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097368B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes