Potassium Acetate → Methyl 3-(acetoxymethyl)-4-nitrobenzoate

HRID 1871951Notes

Reaction equation

HRID 1871951 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7].[C:16]([O-:19])(=[O:18])[CH3:17].[K+]>C(O)(=O)C>[C:16]([O:19][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 10683691Methyl 3-bromomethyl-4-nitrobenzoate

Product 1

HCID 18371998Methyl 3-(acetoxymethyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer and nitrogen inlet, was placed 411 g of the previously prepared methyl 3-bromomethyl-4-nitrobenzoate, 441 g of anhydrous potassium acetate and 2 l of glacial acetic acid. The resulting mixture was refluxed for 4 hours, cooled to room temperature and stirred overnight. Th e solvent was removed in a rotary evaporator and the resulting light yellow solid treated with a mixture of 2 l of ethyl acetate and 1 l of water. The organic phase was separated, washed with water (3×400 mL), brine (1×400 mL) (hied over anhydrous magnesium sulfate and the solvent removed using a rotary evaporator. The crude reaction mixture was triturated with hexane and filtered Yielding 318 g of the expected methyl 3-acetoxymethyl-4-nitrobenzoate. This compound was used as such in the next step.

Workup

  1. customIn a 5-liter three-necked round-bottomed flask equipped with a reflux condenser
  2. temperatureThe resulting mixture was refluxed for 4 hours
  3. customTh e solvent was removed in a rotary evaporator
  4. additionthe resulting light yellow solid treated with a mixture of 2 l of ethyl acetate and 1 l of water
  5. customThe organic phase was separated
  6. washwashed with water (3×400 mL), brine (1×400 mL) (
  7. customthe solvent removed
  8. customa rotary evaporator
  9. customThe crude reaction mixture
  10. customwas triturated with hexane
  11. filtrationfiltered

Sources & evidence

ORD record
ord-5027be7dcd1a4ea7ba9a525da13a174e
Source dataset
uspto-grants-2000_08
Patent number
US06107316

Reaction notes

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