Methanol → Methyl 2-(3-nitrophenyl)acetate

HRID 582052Notes

Reaction equation

HRID 582052 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].[CH3:14]O>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 158763-Nitrophenylacetic acid

Product 1

HCID 526967Methyl 2-(3-nitrophenyl)acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
50 °C

Procedure

Combine (3-nitrophenyl)acetic acid (20.0 g, 110 mmol) and anhydrous methanol (125 mL). Add 7 drops of concentrated sulfuric acid. Heat to 50° C. After 14 hours, cool to ambient temperature. Evaporate in vacuo to give a residue. Partition the residue between water and diethyl ether. Separate the organic layer and extract with aqueous saturated sodium bicarbonate solution and brine. Dry the organic layer over MgSO4 and filter. Slowly evaporate to give methyl (3-nitrophenyl)acetate. 1H NMR (CDCl3) δ 8.17 (d, 1 H, J=1.1 Hz), 8.14 (dd, 1 H, J=1.0, 7.7 Hz), 7.63 (dd, 1 H, J=1.1, 7.7 Hz), 7.52 (t, 1 H, J=7.7 Hz), 3.75 (s, 2 H), 3.73 (s, 3 H).

Workup

  1. temperaturecool to ambient temperature
  2. customEvaporate in vacuo
  3. customto give a residue
  4. customPartition the residue between water and diethyl ether
  5. customSeparate the organic layer
  6. extractionextract with aqueous saturated sodium bicarbonate solution and brine
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customSlowly evaporate

Sources & evidence

ORD record
ord-fd1cc45a9de241f59bbefe37dbeec852
Source dataset
uspto-grants-1999_07
Patent number
US05922752

Reaction notes

Loading…