Pyridine → 2-Oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate

HRID 395669

Reaction equation

HRID 395669 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[C:21](Cl)(=[O:29])[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:21](=[O:29])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:1][CH2:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 112871692-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 129929622-Oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxy-4′-trifluoromethyl acetophenone (24.0 g), pyridine (10.3 g) and tetrahydrofuran (200 ml) was added dropwise phenyl chlorocarbonate (20.4 g) under ice-cooling, which was stirred at room temperature for 1 hour. The reaction mixture was concentrated, which was poured into water (500 ml), and extracted with ethyl acetate (150 ml×2). The organic layer was washed with water and then a saturated aqueous solution of sodium chloride, which was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to crystallization by addition of isopropyl ether (100 ml) to give crystals of 2-oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate (18.9 g, 53%). Melting point 134-135° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionwhich was poured into water (500 ml)
  4. extractionextracted with ethyl acetate (150 ml×2)
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, which was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was subjected to crystallization by addition of isopropyl ether (100 ml)

Sources & evidence

ORD record
ord-e1d0f28c574a4582986d3542d7789975
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Linked notes

Loading…