Pyridine → 1-chloro-4-phenylbutan-4-one O-methyloxime

HRID 1902253Notes

Reaction equation

HRID 1902253 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[Cl-].[CH3:14][O:15][NH3+:16].N1C=CC=CC=1>C(O)C>[CH3:14][O:15][N:16]=[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][CH2:3][CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11639O-methylhydroxylammonium chlorideHCID 2535334-Chlorobutyrophenone

Product 1

HCID 543016361-chloro-4-phenylbutan-4-one O-methyloximeYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-4-phenylbutan-4-one (1.83 g, 10 mmol), O-methylhydroxylammonium chloride (1.67 g, 20 mmol), pyridine (1.21 ml, 15 mmol), and ethanol (15 ml) was heated at reflux for 1 hour and then evaporated in vacuo. The residue was partitioned between chloroform and water, and the organic layer was dried (MgSO4) and evaporated in vacuo to give 1-chloro-4-phenylbutan-4-one O-methyloxime (1.78 g, 84%), νmax (neat) 2930, 1445, 1050, 900 cm-1 ; λmax (EtOH) 209 nm (εm 17,200), 253 nm (εm 11,100); δH (CDCl3) 7.3-7.8 (5H, m, aryl), 3.9 (3H, s, OMe), 3.5 (2H, t, H1), 2.9 (2H, t, H3), 2.0 (2H, qn, H2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customevaporated in vacuo
  4. customThe residue was partitioned between chloroform and water
  5. dry with materialthe organic layer was dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b4b2f4e9308949f7a0fee4e6c1fa4f9d
Source dataset
uspto-grants-1982_12
Patent number
US04362743

Reaction notes

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