Benzyl 3,3-difluoro-2,2-dimethylpropanoate → 3,3-Difluoro-2,2-dimethylpropanoic acid

HRID 520372Notes

Reaction equation

HRID 520372 reaction equation
[F:1][CH:2]([F:16])[C:3]([CH3:15])([CH3:14])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>CCOC(C)=O.[Pd]>[F:1][CH:2]([F:16])[C:3]([CH3:15])([CH3:14])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 86690093Benzyl 3,3-difluoro-2,2-dimethylpropanoate

Product 1

HCID 198673873,3-Difluoro-2,2-dimethylpropanoic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of benzyl 3,3-difluoro-2,2-dimethylpropanoate (340 mg, 1.49 mmol) and 10% Pd—C (42 mg, 0.04 mmol) in EtOAc (20 mL) was hydrogenated under balloon pressure overnight. The suspension was filtered and the filtrate was evaporated to dryness to afford Cap-11 as a white solid (205 mg). 1H NMR (400 MHz, chloroform-d) δ 6.01 (t, J=1.0 Hz, 1H), 2.07 (br. s, 1H), 1.34 (t, J=1.0 Hz, 6H).

Workup

  1. customwas hydrogenated under balloon pressure overnight
  2. filtrationThe suspension was filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-cc61402c183b4a5bbfc890def0dc2fca
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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