Acetic Acid → HCID 808398, compound

HRID 927031Notes

Reaction equation

HRID 927031 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:19][OH:20].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[N:19][OH:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 7358604-[(4-Fluorophenyl)methoxy]benzaldehyde

Product 1

HCID 808398HCID 808398, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a suspension of 4-(4-fluoro-benzyloxy)-benzaldehyde (21.9 g, 95.2 mmol) and hydroxylamine hydrochloride (7.3 g, 105 mmol) in 400 mL water/ethanol 9:1 was added a solution of NaOH (9.5 g in 100 mL of water) dropwise over 15 min. The now yellow solution was stirred for 2 h at rt after which the reaction was adjusted to pH 5-6 with acetic acid. The resulting white precipitate was collected by filtration and washed with water. The wet filter cake was dissolved in ethyl acetate and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave 4-(4-fluoro-benzyloxy)-benzaldehyde oxime (23.5 g, 95.8 mmol) as a yellowish crystalline solid.

Workup

  1. filtrationThe resulting white precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionThe wet filter cake was dissolved in ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration
  6. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-2186f1bb07b04831860db2e8a7d02bd6
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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