Sodium Hydroxide → 2-(4,4-Difluorocyclohexyl)-2-methylpropanoic acid

HRID 920750Notes

Reaction equation

HRID 920750 reaction equation
[F:1][C:2]1([F:16])[CH2:7][CH2:6][CH:5]([C:8]([CH3:15])([CH3:14])[C:9]([O:11]CC)=[O:10])[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1([F:16])[CH2:3][CH2:4][CH:5]([C:8]([CH3:14])([CH3:15])[C:9]([OH:11])=[O:10])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118061258Ethyl 2-(4,4-difluorocyclohexyl)-2-methylpropanoate

Product 1

HCID 896929402-(4,4-Difluorocyclohexyl)-2-methylpropanoic acidYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Intermediate 232B (0.15 g, 0.640 mmol) in ethanol (2 mL) and water (1 mL) was added NaOH (0.256 g, 6.40 mmol) and the reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was acidified with an aqueous solution of 1.5N HCl and extracted with EtOAc (2×20 mL) The combined organic layer was dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 232C as a yellow solid (90 mg, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.20 (br. s., 1H), 2.11-1.94 (m, 2H), 1.91-1.55 (m, 5H), 1.34-1.14 (m, 2H), 1.09-0.96 (m, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×20 mL) The combined organic layer
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0abbb93d1e0d4c919094c0cb10a9515c
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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