Ammonium Chloride → Methyl 2,5-bis(acetoxymethyl)benzoate

HRID 1766855Notes

Reaction equation

HRID 1766855 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Br[CH2:7][C:8]1[CH:17]=[CH:16][C:15]([CH2:18]Br)=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[Cl-].[NH4+]>CS(C)=O>[C:1]([O:4][CH2:7][C:8]1[CH:17]=[CH:16][C:15]([CH2:18][O:4][C:1](=[O:3])[CH3:2])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 517045Sodium AcetateHCID 12633556Methyl 2,5-bis(bromomethyl)benzoate

Product 1

HCID 17862555Methyl 2,5-bis(acetoxymethyl)benzoateYield 70.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium acetate (10.4 g, 126.8 mmol) was added to a solution of methyl 2,5-bis(bromomethyl)benzoate (described in J. Am. Chem. Soc., 121, 1192 (1999); 12.65 g, 39.3 mmol) in dimethyl sulfoxide (80 ml), and the mixture was stirred at room temperature for 1 hour. After a saturated aqueous solution of ammonium chloride (150 ml) was added thereto, the product was extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure. The obtained oily residue was subjected to chromatography on a silica gel (200 g) column (eluent; ethyl acetate:hexane=1:5˜1:2) to afford the title compound (7.72 g, 70% yield) as an oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. distillationwith a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-33d07dc5cf29475faa8a89ab4f932766
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

Loading…