Methanol → Methyl 4-ethyl-3-nitrobenzoate

HRID 514437

Reaction equation

HRID 514437 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:2].O=S(Cl)Cl.[CH3:19]O>>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:19])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 81670864-Ethyl-3-nitrobenzoic acid

Product 1

HCID 21938352Methyl 4-ethyl-3-nitrobenzoateYield 98%

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-ethyl-3-nitrobenzoic acid (5.76 g, 29.53 mmol) in methanol (30 mL) at 0° C., was added SOCl2 (10.54 g, 88.61 mmol) slowly, stirred at this temperature for 1 h, then heated to 50° C. and stirred at this temperature for 3 h. Cooled to room temperature and removed the solvent, the residue was extracted with ethyl acetate, and concentrated to give 6.05 g of the title compound (98%). 1H NMR (400 MHz, CDCl3): δ 1.31 (3H, t, J=7.2 Hz), 2.97 (2H, q, J=7.2 Hz), 3.96 (3H, s), 7.47 (1H, d, J=8.4 Hz), 8.17 (1H, dd, J=1.6, 8.4 Hz), 8.52 (1H, d, J=1.6 Hz).

Workup

  1. stirringstirred at this temperature for 3 h
  2. temperatureCooled to room temperature
  3. customremoved the solvent
  4. extractionthe residue was extracted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0eec74c9de534476b9491859187f4dde
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

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