Methanol → Methyl 2-methyl-3-nitrobenzoate

HRID 1780807Notes

Reaction equation

HRID 1780807 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 160962-Methyl-3-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Procedure

A solution of 2-methyl-3-nitrobenzoic acid (5 g) and thionyl chloride (40 mL) was refluxed for 3 h in methanol (150 mL). The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The ethyl acetate layer was washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated in vacuo to afford the the product as a solid. NMR (300 MHz, CDCl3) δ 7.99 (1H, d), 7.85 (1H, d), 7.38 (1H, t), 3.92 (3H, s), 2.62 (3H, s).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe ethyl acetate layer was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3bc48e12c9446f68131eb4dcf00f0a5
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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