Sulfuric Acid → HCID 13747077, compound

HRID 1761357Notes

Reaction equation

HRID 1761357 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH2:7](O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S(=O)(=O)(O)O>C1C=CC=CC=1.O>[CH2:22]([O:5][C:4](=[O:6])[C@H:2]([CH3:3])[NH2:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 2682Cetyl AlcoholHCID 5950L-Alanine

Product 1

HCID 13747077HCID 13747077, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

4.46 g (0.05 mole) of L-alanine was taken, and 13.3 g (0.055 mole) of cetyl alcohol was taken as an alcohol. After 200 ml of benzene was added thereto as a solvent, these materials were stirred and mixed. After the addition of 4.9 g (0.05 mole) of sulfuric acid as an acid catalyst, the resulting reaction mixture was heated under reflux. In this case, water was formed with the progress of the esterification reaction and released in the form of an azeotropic mixture with benzene, which was continuously removed from the reaction system. Thus, the reaction was completed in about 7 hours (at an internal temperature of 80.5° C.). After being cooled to room temperature, the reaction mixture was poured into a separating funnel and treated with 300 ml of a mixture of 0.2N NaOH and 6% NaCl solutions. This treatment was repeated three times. Thereafter, the benzene layer was isolated and washed thoroughly with water. After washing with water, the benzene layer was isolated and dried overnight over anhydrous sodium sulfate. Thereafter, the benzene layer was filtered and the resulting benzene solution was evaporated to remove the solvent. Thus, there was obtained 13.5 g (86.1% yield) of purified L-alanine cetyl ester in the form of an oily material.

Workup

  1. additionmixed
  2. customthe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux
  5. customwas continuously removed from the reaction system
  6. customat an internal temperature of 80.5° C.
  7. additionthe reaction mixture was poured into a separating funnel
  8. additiontreated with 300 ml of a mixture of 0.2N NaOH and 6% NaCl solutions
  9. customThereafter, the benzene layer was isolated
  10. washwashed thoroughly with water
  11. washAfter washing with water
  12. customthe benzene layer was isolated
  13. dry with materialdried overnight over anhydrous sodium sulfate
  14. filtrationThereafter, the benzene layer was filtered
  15. customthe resulting benzene solution was evaporated
  16. customto remove the solvent

Sources & evidence

ORD record
ord-183b9c4500b94a5b9321d1ce495c7968
Source dataset
uspto-grants-1989_05
Patent number
US04826818

Reaction notes

Loading…