Hydrochloric Acid → Benzaldehyde, 2-fluoro-, oxime

HRID 83191Notes

Reaction equation

HRID 83191 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:11][OH:12].[OH-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N:11][OH:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67970o-FluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 587025Benzaldehyde, 2-fluoro-, oximeYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-fluorobenzaldehyde (63.3 g, 495 mmol) and hydroxylamine hydrochloride (38.2 g, 544 mmol) in ethanol (36 mL) and water (69 mL) was added ice (205 g). Then an aqueous solution of sodium hydroxide (32%, 115 mL, 1.24 mol) was added dropwise within a 10 min period (temperature rises from −8° C. to +7° C.) whereupon most of the solid dissolves. After 1 h stirring at room temperature the resulting mixture was then acidified with HCl (5 N). The mixture was then extracted with dichloromethane to afford the title compound (66.8 g, 97%) which was obtained as a light yellow solid. MS m/e (EI): 139.0 [M].

Workup

  1. dissolutiondissolves
  2. extractionThe mixture was then extracted with dichloromethane

Sources & evidence

ORD record
ord-796b51fae67044e4b73bce12226ac914
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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