Sodium Hydroxide → 3-Nitro-5-(trifluoromethyl)benzaldehyde

HRID 217499Notes

Reaction equation

HRID 217499 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[CH:14]=[O:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 534040393-Nitro-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (400 mg, 1.88 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and then Dess-Martin periodinane (1.59 g, 3.76 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 15% EtOAc/hexanes afforded 3-nitro-5-(trifluoromethyl)benzaldehyde. Rf=0.39 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.18 (s, 1H), 8.91 (s, 1H), 8.74 (s, 1H), 8.48 (s, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc (50 mL)
  2. washthe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 0% to 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-6b3aedaac44646f4a337ed7b73b7d47c
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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