Acetic Acid → 2-butyl trifluoroacetate

HRID 2354252Notes

Reaction equation

HRID 2354252 reaction equation
C=C.C(O)(=O)C.[CH2:7]=[CH:8][CH2:9][CH3:10].[F:11][C:12]([F:17])([F:16])[C:13]([OH:15])=[O:14]>C(OCC)(=O)C>[F:11][C:12]([F:17])([F:16])[C:13]([O:15][CH:8]([CH2:9][CH3:10])[CH3:7])=[O:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6325EthyleneHCID 6422Trifluoroacetic acidHCID 78441-Butene

Product 1

HCID 2447582-butyl trifluoroacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In addition, the esterification of olefins with carboxylic acids and subsequent ester hydrolysis of the alkyl esters formed to the corresponding alcohol with recovery of the acid is known. For instance, U.S. Pat. No. 4,384,148 describes the reaction of ethene with acetic acid to give ethyl acetate in an autoclave. The subsequent hydrolysis of the ethyl acetate removed by distillation with water in a molar ratio of 1:5 in an autoclave affords a mixture comprising ethyl acetate, ethanol and diethyl ether. GB 2 238 539 discloses the two-stage hydration of 1-butene by reaction with trifluoroacetic acid to give 2-butyl trifluoroacetate in the presence of a highly acidic ion exchange resin and subsequent hydrolysis of the ester to give 2-butanol.

Workup

  1. customremoved by distillation with water in a molar ratio of 1:5 in an autoclave
  2. customaffords a mixture comprising ethyl acetate, ethanol and diethyl ether

Sources & evidence

ORD record
ord-4794efa700334bfbb378f61837898ac7
Source dataset
uspto-grants-2010_07
Patent number
US07750194B2

Reaction notes

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