Ethanol → Ethyl 2-methyl-5-nitrobenzoate

HRID 1184918Notes

Reaction equation

HRID 1184918 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH2:25](O)[CH3:26]>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:25][CH3:26])=[O:5]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 18510875Ethyl 2-methyl-5-nitrobenzoateYield 95%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methyl-5-nitrobenzoic acid (27.6 mmol, 5 g) in ethanol (100 mL), sulfuric acid (138 mmol, 7.36 ml) was added slowly and stirred overnight at 80° C. The reaction mixture was neutralized with saturated solution of Na2CO3, extracted with diethyl ether (3×), organic layers were washed with brine, dried and concentrated under reduced pressure to yield crude product ethyl 2-methyl-5-nitrobenzoate 101 (5.4 g, 95%). NMR (400 MHz, CDCl3) 1.44 (t, J=7.0 Hz, 3H), 2.72 (s, 3H), 4.42 (q, J=7.04 Hz, 2H), 7.43 (d, J=8.6 Hz, 1H), 8.23 (dd, J=8.6 Hz and 2.7 Hz, 1H), 8.76 (d, J=2.7 Hz, 1H).

Workup

  1. extractionextracted with diethyl ether (3×), organic layers
  2. washwere washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c3dc3dcd71e457283271ab8dff3bea1
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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