Methanol → Methyl 3-(1-cyanoethyl)benzoate

HRID 2391158Notes

Reaction equation

HRID 2391158 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[CH3:4])#[N:2].S(=O)(=O)(O)O.[CH3:19]O>>[C:1]([CH:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:19])=[O:9])[CH3:4])#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 983703-(1-Cyanoethyl)benzoic acid

Product 1

HCID 10035402Methyl 3-(1-cyanoethyl)benzoateYield 89%

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(1-cyanoethyl)benzoic acid (2.0 g, 11 mmol) in methanol (20 mL) was added conc. sulfuric acid (0.2 mL), and the mixture was stirred at 60° C. for 8 hr. The reaction mixture was concentrated under reduced pressure, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure to give the title compound (1.9 g, 89%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bfe704a13c7345da8e4c092bf5790282
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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