Sodium Hydroxide → [2-Nitro-4-(trifluoromethyl)phenyl]methanol

HRID 230560Notes

Reaction equation

HRID 230560 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19])(=O)C.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>CO>[N+:18]([C:9]1[CH:10]=[C:11]([C:14]([F:15])([F:16])[F:17])[CH:12]=[CH:13][C:8]=1[CH2:7][OH:6])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 68825906HCID 68825906, compound

Product 1

HCID 45790938[2-Nitro-4-(trifluoromethyl)phenyl]methanolYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.9 cm3 (1.9 mmol) of a 1M aqueous sodium hydroxide solution are added, at a temperature in the region of 20° C., to 0.5 g (1.9 mmol) of 2-nitro-4-trifluoromethylbenzyl acetate in solution in 50 cm3 of methanol. After stirring for 2 hours at a temperature in the region of 20° C., 20 cm3 of a saturated aqueous sodium phosphate solution are added and the mixture is then extracted with 3 times 50 cm3 of dichloromethane. The organic phases are combined, washed with 50 cm3 of a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (2.7 kPa), to give 0.424 g of (2-nitro-4-trifluoromethylphenyl)methanol in the form of an oil;

Workup

  1. additionare added
  2. extractionthe mixture is then extracted with 3 times 50 cm3 of dichloromethane
  3. washwashed with 50 cm3 of a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-104c926309524e1988c04b7d1894472b
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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