Trifluoroacetic acid → 26395-06-2

HRID 1077051Notes

Reaction equation

HRID 1077051 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][C:5](=[O:13])[C:6]([O:8]C(C)(C)C)=[O:7].FC(F)(F)C(O)=O.[Na].[OH-].[K+]>>[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][C:5](=[O:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acid4×HCID 14797Potassium HydroxideHCID 5360545SodiumHCID 21535784HCID 21535784, compound

Product 1

HCID 1293965126395-06-2

Procedure

t-Butyl 5-methyl-2-oxohexanoate is readily hydrolyzed under suitably mild conditions at room temperature (i.e., 25°-30° C.). Suitable reactions include hydrolysis directly to the acid form using trifluoracetic acid [reaction (3)] or hydrolysis with dilute bases such as sodium or potassium hydroxide followed by acidification with dilute mineral acids such as hydrochloric, sulfuric, or nitric acids. ##EQU5## Trifluoroacetic acid can be used as a solvent for the reaction shown (3). When trifluoroacetic acid is the hydrolyzing reagent, this step can be accomplished before the hydrogenation step. The acid is recovered by volatization of the trifluoroacetic acid. If hydrolysis is done with dilute base, followed by acidification with mineral acid, the acid is then extracted in the same manner as described for the extraction of the ester in step (a).

Workup

  1. customis readily hydrolyzed under suitably mild conditions at room temperature
  2. custom(i.e., 25°-30° C.)
  3. customhydrolysis directly to the acid form
  4. customThe acid is recovered by volatization of the trifluoroacetic acid
  5. customIf hydrolysis
  6. additionwith dilute base
  7. extractionthe acid is then extracted in the same manner
  8. extractionas described for the extraction of the ester in step (a)

Sources & evidence

ORD record
ord-d21d246030434733949e7fe08fe1a23d
Source dataset
uspto-grants-1976_05
Patent number
US03959312

Reaction notes

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