Sodium Hydroxide → 3,3-Difluoro-3-(4-fluorophenyl)propan-1-ol

HRID 1925535Notes

Reaction equation

HRID 1925535 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)(=O)C.CCCCCC.CC(=O)OCC>CCO>[F:18][C:9]([F:17])([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH2:8][CH2:7][OH:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 67521383Acetic acid [3,3-difluoro-3-(4-fluorophenyl)propyl] ester

Product 1

HCID 671341563,3-Difluoro-3-(4-fluorophenyl)propan-1-olYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 35% aq. NaOH sol. (6 ml) was added to a solution of 1.9 g (8.2 mmol) of 3,3-difluoro-3-(4-fluorophenyl)propyl acetate in EtOH (25 ml), and the mixture was stirred for 2 h at RT. Concentration in vacuo was then carried out and the residue was taken up in water (80 ml). The solution was extracted with EA (3×80 ml) and the combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 9:1) of the residue yielded 1.1 g (5.8 mmol, 71%) of 3,3-difluoro-3-(4-fluorophenyl)propan-1-ol.

Workup

  1. concentrationConcentration in vacuo
  2. extractionThe solution was extracted with EA (3×80 ml)
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11c25982d78242b8b28f3933806127d9
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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