Methanol → Benzoic acid, 3-methyl-2-nitro-, methyl ester

HRID 466743Notes

Reaction equation

HRID 466743 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])([O-:7])=[O:6].[CH3:18]O>>[N+:5]([C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:18])=[O:11])([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 215753-Methyl-2-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Conditions

Temperature
60 °C

Procedure

Thionylchloride (253 mL) was added dropwise to 3 1 methanol at 0°-10° C. Toward end of the addition, the temperature was allowed to rise to 20° C. Solid 2-nitro-3-methylbenzoic acid (500 g) was charged in one portion and the reaction mixture was heated to reflux overnight. It was distilled until pot reached 73° C. After cooling to 60° C., 685 mL water was introduced dropwise and the reaction mixture was cooled to 20° C. Upon adding 26 mL water and 125 mL 80% NaOH, the pH was adjusted to 7. The product was collected by filtration and washed with 3×100 mL water and air dried overnight. Yield of methyl 2-nitro-3-methylbenzoate was 503.5 g (93.5%), mp 72° C.

Workup

  1. additionToward end of the addition
  2. customto rise to 20° C
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux overnight
  5. distillationIt was distilled
  6. customuntil pot reached 73° C
  7. addition685 mL water was introduced dropwise
  8. temperaturethe reaction mixture was cooled to 20° C
  9. additionUpon adding 26 mL water and 125 mL 80% NaOH
  10. filtrationThe product was collected by filtration
  11. washwashed with 3×100 mL water and air
  12. customdried overnight

Sources & evidence

ORD record
ord-40b23a4486ad4775a3c9967e15f48ef6
Source dataset
uspto-grants-1992_10
Patent number
US05157119

Reaction notes

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