Pyridine → 2-benzyloxyacetophenone O-methyloxime

HRID 1085995Notes

Reaction equation

HRID 1085995 reaction equation
N1C=CC=CC=1.[CH2:7]([O:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:25][O:26][NH2:27]>O>[CH3:25][O:26][N:27]=[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 112531252-(Benzyloxy)-1-phenylethan-1-one

Product 1

HCID 541941012-benzyloxyacetophenone O-methyloximeYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of pyridine were added 0.0434 mole (9.77 g) of 2-benzyloxyacetophenone prepared in the first and second paragraphs in Referential Example 1 (Table 1, No. 1) and 4.35 g (0.0521 mole) of O-methylhydroxylamine hydrochloride. The mixture was stirred at room temperature for 2 hours and then at 100° C. for 1 hour. The reaction liquid was cooled down to room temperature, 300 ml of water was added thereto, and the oil layer was separated off. The aqueous layer was extracted with chloroform and the extract was combined with said oil layer, washed with water, dried and distilled under reduced pressure to obtain 10.77 g of 2-benzyloxyacetophenone O-methyloxime.

Workup

  1. customprepared in the first and second paragraphs in Referential Example 1 (Table 1
  2. waitat 100° C. for 1 hour
  3. customThe reaction liquid
  4. temperaturewas cooled down to room temperature
  5. customthe oil layer was separated off
  6. extractionThe aqueous layer was extracted with chloroform
  7. washwashed with water
  8. customdried
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-fbc2bf8017d44237a15500a0c66576a7
Source dataset
uspto-grants-1991_04
Patent number
US05011989

Reaction notes

Loading…