Ethanol → Ethyl 3,5-dimethyl-4-nitrobenzoate

HRID 1282059Notes

Reaction equation

HRID 1282059 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[C:6](C(O)=O)[C:5]=1[CH3:15])([O-:3])=[O:2].Cl.[CH2:17]([OH:19])[CH3:18].C([OH:22])C>>[N+:1]([C:4]1[C:5]([CH3:15])=[CH:6][C:7]([C:11]([O:19][CH2:17][CH3:18])=[O:22])=[CH:8][C:9]=1[CH3:10])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 81670772,4,6-Trimethyl-3-nitrobenzoic acidHCID 21887872Ethanol hydrochloride

Product 1

HCID 18423120Ethyl 3,5-dimethyl-4-nitrobenzoate

Procedure

To a solution of 4-nitromesitylenecarboxylic acid (13 g) in ethanol (50 ml) was added a solution of 28% hydrochloric acid-ethanol (50 ml) and the mixture was refluxed under heating for 2 hr. There action mixture was concentrated and ethyl acetate was added. The mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=9:1) to give the title compound (7.7 g) as pale-brown crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. concentrationThere action mixture was concentrated
  4. additionethyl acetate was added
  5. washThe mixture was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-1b102ef98ceb46559af964c5a00da3b3
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…