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

HRID 450890Notes

Reaction equation

HRID 450890 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

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 219644814-(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-f9a917cc79b0441a8b420d8957665b8c
Source dataset
uspto-grants-2013_07
Patent number
US08487000B2

Reaction notes

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