Sodium Hydroxide → HCID 797883, compound

HRID 929753Notes

Reaction equation

HRID 929753 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.CCO.[OH2:21].Cl.[NH2:23]O.[OH-].[Na+]>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[N:23][OH:21])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 8801194-[(3-Fluorophenyl)methoxy]benzaldehydeHCID 19096565Water ethanol2×

Product 1

HCID 797883HCID 797883, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(3-Fluoro-benzyloxy)-benzaldehyde (which may be prepared as described in Brabanti, E. et al. WO 2007147491 or may be purchased from Matrix Scientific, Columbia, S.C. 29224-5067; 24 g, 78.2 mmol) was taken up in 9:1 EtOH/H2O (200 mL) and hydroxylamine hydrochloride (8.15 g, 117.3 mmol) was added. A solution of NaOH (7.51 g, 187.6 mmol) in 9:1 EtOH/H2O was added dropwise by addition funnel over 30 min. The mixture was heated at reflux for 4 h, then allowed to cool and acidified to pH 5 by adding glacial AcOH (17 mL). The solid was filtered off and dissolved in EtOAc. The organic solution was dried over Na2SO4, filtered, and evaporated to give 4-(3-fluoro-benzyloxy)-benzaldehyde oxime (6.6 g, 25%).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 4 h
  4. temperatureto cool
  5. filtrationThe solid was filtered off
  6. dissolutiondissolved in EtOAc
  7. dry with materialThe organic solution was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-c6609a9b4eed4b5e9cd20691eb36eb12
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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