Sodium Hydroxide → HCID 131735127, compound

HRID 929767Notes

Reaction equation

HRID 929767 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.Cl.[NH2:22][OH:23].[OH-].[Na+]>CCO.O>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[N:22][OH:23])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 211912844-[[2-(Trifluoromethyl)phenyl]methoxy]benzaldehyde

Product 1

HCID 131735127HCID 131735127, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

4-(2-Trifluoromethyl-benzyloxy)-benzaldehyde (which may be prepared as described in Panetta, J. A. et al. U.S. Pat. No. 6,251,928 Column 25; 28.8 g, 102.7 mmol) was combined with 9:1 EtOH/H2O (210 mL) and hydroxylamine hydrochloride (11 g, 158 mmol) was added. A solution of 3.15 M NaOH in 9:1 EtOH/H2O (70 mL, 221 mmol) was added dropwise. The mixture was stirred at room temperature for 2 h and then heated at 50° C. for 1 h. The mixture was partitioned between EtOAc and H2O, and the organic layer was dried, filtered, and evaporated to give 4-(2-trifluoromethyl-benzyloxy)-benzaldehyde oxime (14 g, 46%).

Workup

  1. additionwas added
  2. temperatureheated at 50° C. for 1 h
  3. customThe mixture was partitioned between EtOAc and H2O
  4. customthe organic layer was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9cc4847ee4b342b2888156883586f273
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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