Hydrochloric Acid → N-[(4-tert-butylphenyl)methylidene]hydroxylamine

HRID 1013346Notes

Reaction equation

HRID 1013346 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].[OH-].[Na+].Cl>O.CCO.C(OCC)C>[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[N:2][OH:3])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 703244-tert-ButylbenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1275951N-[(4-tert-butylphenyl)methylidene]hydroxylamine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydroxylamine hydrochloride (4.65 g, 67.4 mmol) was slowly added to a solution of 4-tert-butylbenzaldehyde (10 g, 61.6 mmol) in water (34 ml) and EtOH (7 ml). An aqueous solution of sodium hydroxide (3.6 g, 153 mmol) was slowly added dropwise, so the temperature of the reaction mixture did not exceed 25° C. The reaction mixture was stirred overnight at RT and mixed with diethyl ether. The aqueous phase was neutralised with 0.5 M aq. hydrochloric acid solution and extracted several times with ether. The combined organic phases were dried over magnesium sulphate and the solvent was removed under vacuum. The desired product 4-tert-butylbenzaldehyde oxime was obtained in a yield of 84% of the theoretical amount (9.1 g)

Workup

  1. customdid not exceed 25° C
  2. extractionextracted several times with ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-325fe9873f5948e692113d9b9c163b0f
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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