Methanol → Methyl 2-(3-nitrophenyl)acetate

HRID 440382Notes

Reaction equation

HRID 440382 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 aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4 and filter. Slowly evaporate to give methyl (3-nitrophenyl)acetate. 1H NMR (CDCl3) δ8.17 (d, 1H, J=1.1 Hz), 8.14 (dd, 1H, J=1.0, 7.7 Hz), 7.63 (dd, 1H, J=1.1, 7.7 Hz), 7.52 (t, 1H, J=7.7 Hz), 3.75 (s, 2H), 3.73 (s, 3H).

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 aqueous saturated sodium chloride solution
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customSlowly evaporate

Sources & evidence

ORD record
ord-d2324e1aba454250b618495c8b4e8c22
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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