Acetaldehyde → 2-chloroethanal O-[2-(morpholin-4-yl)ethyl]oxime

HRID 10171

Reaction equation

HRID 10171 reaction equation
[CH:1](=O)[CH3:2].[ClH:4].Cl.[N:6]1([CH2:12][CH2:13][O:14][NH2:15])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[OH-].[Na+]>O>[N:6]1([CH2:12][CH2:13][O:14][N:15]=[CH:2][CH2:1][Cl:4])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 14798Sodium Hydroxide2×HCID 21978765HCID 21978765, compound

Product 1

HCID 738572932-chloroethanal O-[2-(morpholin-4-yl)ethyl]oximeYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of acetaldehyde (0.1 mL of a 50 wt % soln. in water), O-[2-((morpholin-4-yl))ethyl]hydroxylamine dihydrochloride (0.14 g), NaOH (2N, 0.64 mL) and water (5 mL) was stirred at room temperature overnight. The solution was made basic with NaOH (1N) and extracted with dichloromethane. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford 2-chloroethanal O-[2-((morpholin-4-yl))ethyl]oxime (0.13 g, ˜100%), which was used as such.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43d79bad5eef413a95504b9e5c6de2be
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Linked notes

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