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1-Butanol → Butyl 3,3,3-trifluoro-2,2-dimethylpropanoate

HRID 444890
Notes
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Reaction equation

HRID 444890 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:24](O)[CH2:25][CH2:26][CH3:27]>C(Cl)Cl.CN(C=O)C>[CH2:24]([O:5][C:4](=[O:6])[C:3]([CH3:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH2:25][CH2:26][CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 2631-ButanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 198673673,3,3-Trifluoro-2,2-dimethylpropanoic acid

Product 1

HCID 59293743Butyl 3,3,3-trifluoro-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

3,3,3-Trifluoro-2,2-dimethyl-propionic acid (3.0 g, 19.2 mmol) and a drop of DMF are dissolved in 30 mL of DCM and treated dropwise at RT with oxalyl chloride (1.85 mL, 21.1 mmol). After 2 h gas evolution ceases and the mixture is treated slowly with triethyl amine (5.36 mL, 38.4 mmol) followed by n-butanol (2.1 mL, 23 mmol). The mixture is stirred over night, the solvent evaporated and the residue stirred with hexanes. The solid is filtered off and the filtrate is evaporated to a brown-red oil. Kugelrohr distillation (10 mbar, 60-80° C. oven temperature) gives the title compound a colorless liquid.

Workup

  1. customthe solvent evaporated
  2. stirringthe residue stirred with hexanes
  3. filtrationThe solid is filtered off
  4. customthe filtrate is evaporated to a brown-red oil
  5. distillationKugelrohr distillation (10 mbar, 60-80° C. oven temperature)

Sources & evidence

ORD record
ord-06f6d7056e584c06870e6d37842539a8
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes