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

HRID 370018Notes

Reaction equation

HRID 370018 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. The 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) dried 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. customThe 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. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent removed
  9. customa rotary evaporator
  10. customThe crude reaction mixture
  11. customwas triturated with hexane
  12. filtrationfiltered

Sources & evidence

ORD record
ord-0b5ad20734384fd89647054154a589f5
Source dataset
uspto-grants-2000_10
Patent number
US06140362

Reaction notes

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