Acetone → HCID 54490127, compound

HRID 442728Notes

Reaction equation

HRID 442728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([C:7]1[C:12]([O:13]COC)=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:17])=[O:6].S(=O)(=O)(O)O.CC(C)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([C:7]1[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:17])=[O:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 544656892-(3-Bromobenzoyl)-3-methoxymethoxy pyridine 1-oxide

Product 1

HCID 54490127HCID 54490127, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(3-bromobenzoyl)-3-methoxymethoxy pyridine 1-oxide (4.00 g), 3.6N-sulfuric acid (11 mL) and acetone (50 mL) was refluxed for 5 hours. The reaction mixture was poured into water, neutralized with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, successively, and dried (sodium sulfate) and then concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromobenzoyl)-3-hydroxypyridine 1-oxide (2.81 g). Physical properties and spectrum data of the product are shown below.

Workup

  1. temperaturewas refluxed for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous saline solution, successively, and dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

Sources & evidence

ORD record
ord-0f53dc830e62415bae482296c2c1df32
Source dataset
uspto-grants-1999_04
Patent number
US05891895

Reaction notes

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