Ethanol → 4,4,4-trifluoro-3,3-dimethylbutanoic acid

HRID 1971636Notes

Reaction equation

HRID 1971636 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([CH:6](C(OCC)=O)[C:7]([O:9]CC)=[O:8])([CH3:5])[CH3:4].[OH-].[K+].CCO>>[F:1][C:2]([F:17])([F:18])[C:3]([CH3:5])([CH3:4])[CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22743911HCID 22743911, compound

Product 1

HCID 594961354,4,4-trifluoro-3,3-dimethylbutanoic acidYield 77.2%

Procedure

A solution of diethyl 2-(1,1,1-trifluoro-2-methylpropan-2yl)malonate (iv, 20.93 g, 77.45 mmol) and KOH (17.23 g, 307.1 mmol) in EtOH (200 mL, 3000 mmol) was heated at 80° C. for 16 h. The reaction was concentrated and partitioned between water and Et2O. The aqueous layer was acidified with 6 N HCl and then extracted with Et2O (2×). The organic layers were combined, dried over MgSO4, filtered and concentrated to provide and orange oil. A low pressure distillation gave the product as a light pink liquid (10.17 g, 77%).

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between water and Et2O
  3. extractionextracted with Et2O (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide
  8. distillationA low pressure distillation

Sources & evidence

ORD record
ord-a69f7c3a867745d9ae4c93d2facbb7a1
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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