Hydrochloric Acid → Benzaldehyde, 2-fluoro-, oxime

HRID 1897088Notes

Reaction equation

HRID 1897088 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-f3ecc2470a87484eb822d88f7c5fcb49
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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