Sodium Hydroxide → (2-(Fluoromethyl)-1,3-dioxan-2-yl)methanol

HRID 1645611Notes

Reaction equation

HRID 1645611 reaction equation
C([O:9][CH2:10][C:11]1([CH2:17][F:18])[O:16][CH2:15][CH2:14][CH2:13][O:12]1)(=O)C1C=CC=CC=1.[OH-].[Na+].[Cl-].[NH4+]>CO>[F:18][CH2:17][C:11]1([CH2:10][OH:9])[O:16][CH2:15][CH2:14][CH2:13][O:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 59792542(2-(Fluoromethyl)-1,3-dioxan-2-yl)methyl benzoate

Product 1

HCID 59792600(2-(Fluoromethyl)-1,3-dioxan-2-yl)methanolYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2-(fluoromethyl)-1,3-dioxan-2-yl)methyl benzoate (2.22 g, 8.73 mmol), methanol (20 ml) and a 1N-aqueous sodium hydroxide solution (13.1 ml) was stirred at room temperature overnight. Ammonium chloride was added to the reaction mixture, which was concentrated. The residue was suspended in tetrahydrofuran and ethyl acetate, and then magnesium sulfate was added and the mixture was stirred for 5 minutes. After NH silica gel filtration was performed, the filtrate was concentrated to obtain the title compound (1.17 g, 89.3%) as a colorless liquid.

Workup

  1. concentrationwas concentrated
  2. additionethyl acetate, and then magnesium sulfate was added
  3. filtrationAfter NH silica gel filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0ee37fa47a9b41d9a492c7e522011970
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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