Benzaldehyde → (Z)-Benzaldehyde oxime

HRID 1375627Notes

Reaction equation

HRID 1375627 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-b5169c0354a244a4be8de985aaa456bc
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Reaction notes

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