Methyl 2-ethyl-5-nitrobenzoate → 2-Ethyl-5-nitrobenzoic acid

HRID 47442Notes

Reaction equation

HRID 47442 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH3:14]>CO>[CH2:13]([C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[C:3]([OH:15])=[O:2])[CH3:14]

Participants

3

Reactant 1

HCID 54220219Methyl 2-ethyl-5-nitrobenzoate

Product 1

HCID 227451732-Ethyl-5-nitrobenzoic acidYield 48.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl-5-nitrobenzoic acid methyl ester (1.0 g) in methanol/2N sodium hydroxide (60 ml, 1:1) was stirred for 1 h at 60° C. Half the solvent was removed at reduced pressure, the residue diluted with water (20 ml), washed with dichloromethane and the aqueous phase acidified with 2N HCl. The acidic phase was extracted with dichloromethane, the combined extracts dried (MgSO4) and solvent removed at reduced pressure to give the title compound (0.45 g) as a colourless solid. 1H NMR (CDCl3) δ: 1.32 (3H, t, J=7.6 Hz), 3.19 (2H, q, J=7.6 Hz), 7.52 (1H, d, J=8.4 Hz), 8.33 (1H, dd, J=2.5, 8.4 Hz), 8.90 (1H, d, J=2.5 Hz).

Workup

  1. customHalf the solvent was removed at reduced pressure
  2. additionthe residue diluted with water (20 ml)
  3. washwashed with dichloromethane
  4. extractionThe acidic phase was extracted with dichloromethane
  5. dry with materialthe combined extracts dried (MgSO4) and solvent
  6. customremoved at reduced pressure

Sources & evidence

ORD record
ord-16125d7c6eae4f6fa036d4a2f1bb8cbc
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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