Hydrochloric Acid → Benzaldehyde, 2,4-dihydroxy-, oxime

HRID 1271826Notes

Reaction equation

HRID 1271826 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)C.Cl.[NH2:13][OH:14].[OH-].[Na+].Cl>O.C(O)C>[OH:14][N:13]=[CH:9][C:3]1[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=1[OH:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 94842Benzaldehyde, 2,4-dihydroxy-, oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2.0 grams (0.013 mole) of 1-(2,4-dihydroxyphenyl)ethan-1-one (commercially available) and 1.4 grams (0.019 mole) of hydroxylamine hydrochloride in 20 mL of water and 100 mL of ethanol was cooled to about 0° C. to 4° C. and 2.7 grams (0.068 mole) of sodium hydroxide was added. Upon completion of addition the reaction mixture was warmed to reflux where it stirred during a 30 minute period. After this time the reaction mixture was cooled to ambient temperature and 400 mL of aqueous 5% hydrochloric acid was added. The mixture was extracted with diethyl ether, and the extract was washed with water. The organic layer was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, yielding 1.5 grains of the subject compound.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas warmed
  3. temperatureto reflux where it
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe extract was washed with water
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customyielding 1.5 grains of the subject compound

Sources & evidence

ORD record
ord-a6ceff7e4b434e6992e981ae8fe98a44
Source dataset
uspto-grants-2007_04
Patent number
US07208450B2

Reaction notes

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