Gamma-Aminobutyric Acid → HCID 86691668, compound

HRID 538895Notes

Reaction equation

HRID 538895 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](O)[CH:9]=[CH2:10].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=O)=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:10][CH:9]=[CH2:8])=[O:6])(=[O:20])=[O:21])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 6101p-Toluenesulfonic acidHCID 7858Allyl Alcohol

Product 1

HCID 86691668HCID 86691668, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

γ-Aminobutyric acid (25.8 g, 250 mmol), allyl alcohol (100 mL, 1.50 mol) and p-toluenesulfonic acid (48.5 g, 255 mmol) were suspended in 100 mL of toluene and the suspension was refluxed for 16 h under a water separator. Subsequently, the orange solution was concentrated under reduced pressure. Following complete crystallization of the residue, it was thoroughly washed with diethyl ether (4×300 ml). The product was obtained as a colorless solid (77.8 g, 99%).

Workup

  1. temperaturethe suspension was refluxed for 16 h under a water separator
  2. concentrationSubsequently, the orange solution was concentrated under reduced pressure
  3. customcrystallization of the residue, it
  4. washwas thoroughly washed with diethyl ether (4×300 ml)

Sources & evidence

ORD record
ord-d6f2b0ad49e249f7971cbbec9fc2d55d
Source dataset
uspto-grants-2014_10
Patent number
US08865863B2

Reaction notes

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