Methyl 3-(acetoxymethyl)-4-nitrobenzoate → Methyl 3-(hydroxymethyl)-4-nitrobenzoate

HRID 1740560Notes

Reaction equation

HRID 1740560 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:9]([O:11][CH3:12])=[O:10])(=O)C>CO>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 1

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

Product 1

HCID 18372008Methyl 3-(hydroxymethyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 5-liter three-necked round-bottomed flask equipped with a reflux condenser, overhead stirrer and nitrogen inlet, was placed 318 g of the previously prepared methyl 3-acetoxymethyl-4-nitrobenzoate and 3.2 l of anhydrous methanol. To the resulting solution was bubbled in 40 g of hydrogen chloride and the resulting mixture was refluxed for 3 hours. After cooling to room temperature the solvent was removed using rotary evaporator yielding 273 g of methyl 3-hydroxymethyl-4-nitrobenzoate as a yellow solid containing traces of methanol, which 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. customTo the resulting solution was bubbled in 40 g of hydrogen chloride
  3. temperaturethe resulting mixture was refluxed for 3 hours
  4. customwas removed
  5. customevaporator

Sources & evidence

ORD record
ord-0e42ebf0df6541d88cc3a416587d1b58
Source dataset
uspto-grants-1999_10
Patent number
US05969200

Reaction notes

Loading…