Pyridine → Glycidyl benzoate

HRID 493368Notes

Reaction equation

HRID 493368 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]1[O:12][CH:11]1[CH2:13][OH:14].N1C=CC=CC=1>ClCCl>[C:1]([O:14][CH2:13][CH:11]1[CH2:10][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 11164Glycidol

Product 1

HCID 25998Glycidyl benzoateYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (1.2 mL, 10.0 mmol) was added to a solution of glycidol (0.67 mL, 10.0 mmol) and pyridine (0.81 mL, 10.0 mmol) in anhydrous dichloromethane at 0° C. The reaction mixture was further stirred at 0° C. for 60 min. The reaction mixture was then concentrated to dryness under reduced pressure, diluted with ethyl acetate, and washed with 10% citric acid twice followed by the addition of a saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and concentrated to dryness to yield 1.8 g (100%) of Oxiran-2-ylmethyl benzoate.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with 10% citric acid
  4. additiontwice followed by the addition of a saturated NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b1b61786359d472c9f866df042ebf831
Source dataset
uspto-grants-2009_05
Patent number
US07534813B2

Reaction notes

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