Sodium Hydroxide → Benzaldehyde, 2-(trifluoromethoxy)-, oxime

HRID 1748149Notes

Reaction equation

HRID 1748149 reaction equation
[OH-:1].[Na+].[NH2:3]O.Cl.[F:6][C:7]([F:18])([F:17])[O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O>O.C(O)C>[F:6][C:7]([F:18])([F:17])[O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1/[CH:11]=[N:3]/[OH:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27771922-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 58138479Benzaldehyde, 2-(trifluoromethoxy)-, oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a solution of sodium hydroxide (7 g, 175.00 mmol, 1.19 equiv) in water (120 mL) was added a stirred solution of NH2OH.HCl (11.8 g, 169.78 mmol, 1.15 equiv) in water (120 mL) at 0°C. The resulting solution was stirred fo(10 min at 0°C. Then a solution of 2-(trifluoromethoxy)benzaldehyde (28 g, 147.29 mmol, 1.00 equiv) in ethanol (120 mL) was added. The resulting solution was allowed to stir for an additional 1 h at room temperature. The resulting solution was diluted with 500 ml of H2O, extracted with 2×700 mL of ethyl acetate and the organic layers were combined, washed with 2×300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give (E)-2-(trifluoromethoxy)benzaldehyde oxime as an off-white crystalline solid.

Workup

  1. custom10 min
  2. customat 0°C
  3. stirringto stir for an additional 1 h at room temperature
  4. extractionextracted with 2×700 mL of ethyl acetate
  5. washwashed with 2×300 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8a9155f18df84d49b08717ca4f761ba2
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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