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Hydrochloric Acid → 3,3'-Difluorobenzophenone oxime

HRID 25189
Notes
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Reaction equation

HRID 25189 reaction equation
Cl.[NH2:2][OH:3].[F:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)=O.[OH-].[Na+].Cl>O.C(O)C>[F:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8](=[N:2][OH:3])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5795023,3'-Difluorobenzophenone

Product 1

HCID 225067163,3'-Difluorobenzophenone oximeYield 96.7%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

3-3′-Difluorobenzophenone oxime may be prepared according to the following procedure: a solution of 1.6 g of hydroxylamine hydrochloride in 8 cm3 of water is poured dropwise into a solution of 5.0 g of 3,3′-difluorobenzophenone in 10 cm3 of ethanol, and then 1.2 g of sodium hydroxide pellets are added in small fractions. The reaction mixture, heated under reflux for 10 minutes, is cooled to 20° C. and then acidified with 7.5 cm3 of 4 N hydrochloric acid. Once triturated, the oily precipitate obtained becomes a white solid which is filtered, washed with water and then dried at 35° C. under reduced pressure (2.7 kPa). 5.17 g of 3,3′-difluorobenzophenone oxime are obtained in the form of a white solid.

Workup

  1. temperatureThe reaction mixture, heated
  2. temperatureunder reflux for 10 minutes
  3. customOnce triturated
  4. customthe oily precipitate obtained
  5. filtrationis filtered
  6. washwashed with water
  7. customdried at 35° C. under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ee5dc6e2dbd94dac964b2f5403955c49
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858603B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes