Benzyl Alcohol → HCID 86183876, compound

HRID 2299232Notes

Reaction equation

HRID 2299232 reaction equation
[NH2:1]C(CC)C(O)=O.[CH2:8]([OH:15])[C:9]1C=CC=[CH:11][CH:10]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.[OH2:27]>C1C=CC=CC=1>[CH2:26]([O:27][C:8](=[O:15])[CH2:9][CH:10]([NH2:1])[CH3:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6657Alpha-Aminobutyric Acid

Product 1

HCID 86183876HCID 86183876, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

According to the above synthetic scheme, first, 18.1 g of aminobutyric acid, 87.5 ml of benzyl alcohol and 40.0 g of p-toluenesulfonic acid were dissolved in 175 ml of benzene and refluxed. The water formed was removed as the azeotrope with benzene. To the reaction solution were added 280 ml of diethyl ether and 280 ml of hexane to form a precipitate. This precipitate was separated by filtration and recystallized in an ether/ethanol mixed solution to effect purification. As a result, 53.8 mg of β-aminobutyric acid benzyl ester·p-toluenesulfonate were obtained as a white crystal. From the results of 1H-NMR spectrometry the synthesis of β-aminobutyric acid benzyl ester·p-toluenesulfonate was confirmed. The results of the 1H-NMR spectrometry are set forth below. The underlined portion shows the position of the corresponding proton in the compound. Further, in the NMR data, “Φ-” shows a phenyl group.

Workup

  1. temperaturerefluxed
  2. customwas removed as the azeotrope with benzene
  3. additionTo the reaction solution were added 280 ml of diethyl ether and 280 ml of hexane
  4. customto form a precipitate
  5. customThis precipitate was separated by filtration
  6. customrecystallized in an ether/ethanol mixed solution to effect purification

Sources & evidence

ORD record
ord-cb57524bbbf14a0297f1a62a31b90695
Source dataset
uspto-grants-2002_12
Patent number
US06495645B1

Reaction notes

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