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Hydrochloric Acid → 4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-oxobutanecarbohydroxamic acid

HRID 25029
Notes
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Reaction equation

HRID 25029 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[CH3:6][C:7]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:8]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:17](=[O:25])[CH2:18][CH2:19][C:20](OCC)=O)[CH:14]=[CH:15][CH:16]=1.Cl.[CH2:32]([OH:34])C>O>[CH3:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:7]([CH3:6])[C:8]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:17](=[O:25])[CH2:18][CH2:19][CH2:20][C:32]([NH:2][OH:3])=[O:34])[CH:14]=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14797Potassium Hydroxide2×HCID 443297Hydroxyamine hydrochlorideHCID 21964476Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxobutyrate

Product 1

HCID 21964481
4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-oxobutanecarbohydroxamic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a hydroxylamine hydrochloride solution in dry ethanol, add a solution of potassium hydroxide in dry ethanol at 35° C. Cool the mix and add Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxobutyrate (Step C), and powdered potassium hydroxide. After few hours, reaction mixture can be diluted with water and neutralize with hydrochloric acid, filter and recrystallize to give title compound.

Workup

  1. temperatureCool the
  2. additionmix
  3. waitAfter few hours
  4. customreaction mixture
  5. filtrationfilter
  6. customrecrystallize

Sources & evidence

ORD record
ord-f9243e2552d44325ac8cb1979881d94a
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858602B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes