Ethanol → HCID 136209487, compound

HRID 846004Notes

Reaction equation

HRID 846004 reaction equation
Cl.[CH2:2]([O:5][NH2:6])[CH:3]=[CH2:4].[OH-].[Na+].[C:9]([C:14]1[C:15](=[O:30])[CH2:16][CH:17]([C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[CH3:29])[CH2:18][C:19]=1[OH:20])(=O)[CH2:10][CH2:11][CH3:12].C(O)C>O>[CH2:2]([O:5][N:6]=[C:9]([C:14]1[C:19](=[O:20])[CH2:18][CH:17]([C:21]2[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])[CH2:16][C:15]=1[OH:30])[CH2:10][CH2:11][CH3:12])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 178450313HCID 178450313, compound

Product 1

HCID 136209487HCID 136209487, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Allyloxyamine hydrochloride (0.72 g) and then a solution of sodium hydroxide (0.25 g) in water (3 ml) were added to a stirred mixture of 2-butyryl-3-hydroxy-5-mesitylcyclohex-2-en-1-one (1.78 g; 5.9 mmole) and 95% ethanol. The progress of the reaction was monitored using thin layer chromatography on silica gel (eluant dichloromethane). On completion of the reaction the ethanol was removed by evaporation using a rotary evaporator and the residue was extracted with dichloromethane. The organic extract was washed with aqueous 5% hydrochloric acid and then with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure using a rotary evaporator to give the product, 2-[1-(allyloxyimino)butyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (1.6 g) as an oil.

Workup

  1. customwas removed by evaporation
  2. customa rotary evaporator
  3. extractionthe residue was extracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with aqueous 5% hydrochloric acid
  6. dry with materialwith water and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-c2821e1a91aa45369a7a32da6bd199da
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

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