Acetic Acid → HCID 131735044, compound

HRID 927028Notes

Reaction equation

HRID 927028 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[NH2:20][OH:21].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[N:20][OH:21])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 41542764-[(4-methoxybenzyl)oxy]benzaldehyde

Product 1

HCID 131735044HCID 131735044, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Conditions

Temperature
88 °C

Procedure

To a suspension of 4-(4-methoxy-benzyloxy)-benzaldehyde (26.5 g, 110 mmol) in water/ethanol (260 mL, 9:1) was added hydroxylamine hydrochloride (9.06 g, 131 mmol) followed by dropwise addition of a 3.2M NaOH solution in ethanol/water (88 mL; 262 mmol). After addition was complete, the reaction mixture was heated to 88° C. for 4.5 h and then cooled to rt. The pH of the reaction mixture was adjusted to 5.5 with glacial acetic acid. 4-(4-methoxy-benzyloxy)-benzaldehyde oxime (23.8 g, 84%) was isolated as a white solid by filtration and air drying.

Workup

  1. additionAfter addition
  2. temperaturecooled to rt

Sources & evidence

ORD record
ord-9fb11eb5867a4b12bed98981cc9fbaf2
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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