Methanol → HCID 58524150, compound

HRID 536431Notes

Reaction equation

HRID 536431 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:19]O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:19])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 111715593,4-Dimethyl-2-nitrobenzoic acid

Product 1

HCID 58524150HCID 58524150, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,4-dimethyl-2-nitrobenzoic acid (13 g) and thionyl chloride (11.8 g) in toluene (100 ml) was refluxed for 4 h. The reaction mixture was cooled at 0° C., treated with methanol (15 ml) and the solvent was removed under vacuum. The reaction mixture was treated water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over sodium sulfate and concentrated to give methyl 3,4-dimethyl-2-nitrobenzoate (10 g). 1H-NMR (400 MHz, CDCl3): 2.19 (s, 3H), 2.38 (s, 3H), 3.87 (s, 3H), 7.25 (d, 1H), 7.79 (d, 1H).

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe reaction mixture was treated water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43f000fcb124444bafb5e0500ea81acf
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

Loading…