Gamma-Butyrolactone → N-Decyl-4-hydroxybutyramide

HRID 477429Notes

Reaction equation

HRID 477429 reaction equation
[CH2:1]([NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12]1(=[O:17])[O:16][CH2:15][CH2:14][CH2:13]1>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH2:1]([NH:11][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 7302Gamma-ButyrolactoneHCID 8916Decylamine

Product 1

HCID 11139345N-Decyl-4-hydroxybutyramideYield 44.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 15 g of decylamine, 5.48 g of gamma butyrolactone, 100 ml of toluene, and 20 mg of zinc chloride was refluxed under nitrogen for 4 days. Upon cooling the reaction mixture formed a precipitate which was recrystallized from toluene to yield 6.91 g (44.6%) of N-decyl-4-hydroxybutyramide, m.p. 74-75° C.

Workup

  1. temperaturewas refluxed under nitrogen for 4 days
  2. temperatureUpon cooling the reaction mixture
  3. customformed a precipitate which
  4. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-a98c048cd37d43429dbfbdf02c83f7fc
Source dataset
uspto-grants-1989_12
Patent number
US04888328

Reaction notes

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