Benzaldehyde → (Z)-Benzaldehyde oxime

HRID 2120850Notes

Reaction equation

HRID 2120850 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:10][OH:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O.[Cl-].[Na+].O>[CH:1](=[N:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 12143(Z)-Benzaldehyde oximeYield 96.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To benzaldhyde (10.0 g, 94 mmol) in ethanol (50 mL) was added hydroxylamine hydrochloride (6.5 g, 94 mmol in H2O (50 mL) followed by Na2CO3 in H2O (50 mL). Reaction solution was stirred for 2 hr. Poured into brine and extracted twice with diethyl ether. Combined extracts were dried over MgSO4. Evaporation afforded benzaldehyde oxime (11.0 g, 96.5% yield) as a colorless oil. 1H NMR (CDCl3) δ 7.40-7.50 (m, 3H), 7.60-7.70 (m, 2H) 8.22 (s, 1H), 9.1 (bs, 1H).

Workup

  1. customReaction solution
  2. extractionextracted twice with diethyl ether
  3. dry with materialCombined extracts were dried over MgSO4
  4. customEvaporation

Sources & evidence

ORD record
ord-a6c62cce31ff44daaf42defefd00f6c6
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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