Methanol → Methyl 3-hydroxy-2-nitrobenzoate

HRID 1672460Notes

Reaction equation

HRID 1672460 reaction equation
O=S(Cl)Cl.[CH3:5]O.[OH:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12]>C(OCC)(=O)C>[OH:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([O:13][CH3:5])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2932913-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 13659833Methyl 3-hydroxy-2-nitrobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

SOCl2 (0.6 mL) was added dropwise to anhydrous MeOH (10 mL) at 0° C. The mixture was stirred at this temperature for 0.5 h, then 3-hydroxy-2-nitrobenzoic acid (0.6 g, 3.2 mmol) was added to the mixture. The resulting mixture was heated at reflux for 4 h. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete. The resulting mixture was concentrated in vacuo to give the title compound (0.63 g 100%) as a brown solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cb4588a5ee634045badc686a639fc89f
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

Loading…