Hydrochloric Acid → N-Butyl-12-hydroxyoctadecanamide

HRID 745471

Reaction equation

HRID 745471 reaction equation
[OH:1][CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=O.C[O-].[Na+].[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29].Cl>CO>[CH2:26]([NH:30][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([OH:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 8840Methyl 12-hydroxystearateHCID 10942334Sodium Methoxide

Product 1

HCID 54454815N-Butyl-12-hydroxyoctadecanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

50 g of methyl 12-hydroxystearate, 300 ml of methanol and 20 ml of a 28% methanol solution of sodium methoxide were mixed, and 50 ml of n-butylamine was added thereto. The resulting mixture was heat-refluxed for 6.5 hours. After cooling, the reaction mixture was poured into dilute hydrochloric acid, and the precipitated crystals were filtered to obtain 47 g of N-butyl-12-hydroxystearic acid amide having a melting point of 100°-102° C.

Workup

  1. temperatureThe resulting mixture was heat-refluxed for 6.5 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-14df8a9097a245a380c264b65c1ccb0e
Source dataset
uspto-grants-1986_07
Patent number
US04599296

Linked notes

Loading…