Methanol → Methyl (3-cyanophenyl)acetate

HRID 1428701Notes

Reaction equation

HRID 1428701 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].S(=O)(=O)(O)O.[CH3:18]O>>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:18])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15193972-(3-Cyanophenyl)acetic acid

Product 1

HCID 1514291Methyl (3-cyanophenyl)acetateYield 84%

Conditions

Temperature
70 °C

Procedure

To the solution 2-(3-cyanophenyl)acetic acid (700 mg, 43.4 mmol) in methanol was slowly added sulfuric acid (0.42 mL, 4.34 mmol) at room temperature. The reaction mixture was refluxed for 3 h at 70° C. under nitrogen atmosphere. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature. Solvent was removed in vacuo and extracted with ethyl acetate. The organic part was washed with brine and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford crude product which was purified by column chromatography to afford methyl 2-(3-cyanophenyl)acetate (660 mg, 84%).

Workup

  1. customat room temperature
  2. customconsumption of starting material
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customSolvent was removed in vacuo
  5. extractionextracted with ethyl acetate
  6. washThe organic part was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto afford crude product which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4be635770bcd4c99bc5f4d336aa176e4
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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