Benzyl Alcohol → Benzyl 2-cyanoacetate

HRID 229493Notes

Reaction equation

HRID 229493 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7](O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:7]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 9740Cyanoacetic acid

Product 1

HCID 560818Benzyl 2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of cyanoacetic acid (VII) 2.34 g (27.5 mmol) and benzyl alcohol (VIIIa) 2.70 g (25 mmol) in 60 mL of toluene 50 mg of p-TsOH was added and the mixture was refluxed in a flask with a Dean-Stark trap for 24 h. The mixture was cooled down and toluene was washed with H2O and toluene was evaporated. The residue was distilled in vacuo (Kugelrohr apparatus, 0.1 mm Hg, T. oven 170-180° C.). Yield 3.36 g (77%), a colorless oil. MS (m/z, rel. intensity, %): 167.0 ([M+NH4−CN]+, 27), 193.0 ([M+NH4]+, 100).

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed in a flask with a Dean-Stark trap for 24 h
  3. temperatureThe mixture was cooled down
  4. washtoluene was washed with H2O and toluene
  5. customwas evaporated
  6. distillationThe residue was distilled in vacuo (Kugelrohr apparatus, 0.1 mm Hg, T. oven 170-180° C.)

Sources & evidence

ORD record
ord-e39c70ae93a8455da1ace198e8eb0052
Source dataset
uspto-grants-2009_07
Patent number
US07563820B2

Reaction notes

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