Pyridine → Benzoic acid, acetylmethyl ester

HRID 31586

Reaction equation

HRID 31586 reaction equation
N1C=CC=CC=1.C1COCC1.[OH:12][CH2:13][C:14](=[O:16])[CH3:15].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:17]([O:12][CH2:13][C:14](=[O:16])[CH3:15])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8299Hydroxyacetone

Product 1

HCID 23137Benzoic acid, acetylmethyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a pyridine (25 ml) and THF (10 ml) solution of hydroxyacetone (5 g, 67.5 mmol), benzoyl chloride (12 ml, 103 mmol) was added dropwise at 0° C. in a nitrogen atmosphere and the mixture was stirred for 43 hours at room temperature. Ice was added to the reaction mixture, which was then diluted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient). Desired fractions were concentrated to obtain the title compound (10.56 g, 87.8% yield) as a light yellow oil.

Workup

  1. additionIce was added to the reaction mixture, which
  2. washThe organic layer was washed with 1N hydrochloric acid, water
  3. dry with materiala saline solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient)
  7. concentrationDesired fractions were concentrated

Sources & evidence

ORD record
ord-dd0a4ec0dabe404984930a4985ccb38e
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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