Beta-Propiolactone → n-dodecyl-2-hydroxypropanamide

HRID 1449425Notes

Reaction equation

HRID 1449425 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[O:14]1CC[O:17][CH2:16][CH2:15]1.[C:20]1(=O)OCC1>CCCCCC>[CH2:1]([NH:13][C:16](=[O:17])[CH:15]([OH:14])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 2365Beta-PropiolactoneHCID 13583DodecylamineHCID 312751,4-Dioxane

Product 1

HCID 223435n-dodecyl-2-hydroxypropanamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

25.34 g (0.1367 mol) of dodecylamine and 30 g of dioxane were fed into a 200-ml four-necked flask equipped with a stirrer, a dropping funnel and a thermometer to thereby prepare a transparent solution. Then, 9.85 g (0.1367 mol) of β-propiolactone was dropwise added to the transparent solution over a period of about 15 min. During this period, the temperature of the reaction system was maintained at 25° to 30° C. The obtained reaction mixture was further stirred at 30° C. for 5 hrs. The obtained crude product having a temperature of its melting point or above was dropwise added to 100 ml of hexane to crystallize. Thus, 28.93 g of N-dodecyl-2-hydroxypropionamide was obtained (yield: 82%). The infrared absorption spectrum data and 1H-NMR spectrum data of the obtained compound were as follows:

Workup

  1. customequipped with a stirrer, a dropping funnel
  2. customa thermometer to thereby prepare a transparent solution
  3. waitDuring this period
  4. temperaturethe temperature of the reaction system was maintained at 25° to 30° C
  5. customThe obtained reaction mixture
  6. customThe obtained crude product
  7. customto crystallize

Sources & evidence

ORD record
ord-04fef72998f64db7b330cbe9dedc31f5
Source dataset
uspto-grants-1997_02
Patent number
US05599483

Reaction notes

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