Hydrochloric Acid → Methyl 2-(3-nitrophenyl)acetate

HRID 1696457Notes

Reaction equation

HRID 1696457 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:15]O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 158763-Nitrophenylacetic acid

Product 1

HCID 526967Methyl 2-(3-nitrophenyl)acetateYield 96%

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 3-nitrophenylacetic acid (10.4 g, 57.3 mmol) in MeOH (250 ml) at RT was added HCl gas until saturation was achieved. The resulting solution was stirred at 70° C. for 1 h. The reaction was cooled and concentrated under reduced pressure. The semisolid residue was dissolved in Et2O, washed with H2O (2×), satd. NaHCO3 (2×), brine (1×) and dried (MgSO4). Filtration and evaporation provided methyl 2-(3-nitrophenyl)acetate as a low-melting solid (10.7 g, 96% yield), which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 8.14-8.04 (m, 2H), 7.64-7.58 (m, 1H), 7.47 (brt, J=8.10 Hz, 1H), 3.72 (s, 2H), 3.68 (s, 3H); MS (ESI) m/z: 196.0 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe semisolid residue was dissolved in Et2O
  4. washwashed with H2O (2×)
  5. dry with materialNaHCO3 (2×), brine (1×) and dried (MgSO4)
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-6f68b91269bb4f909d852812440fb4ef
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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