Glycidol → 1,2-Propanediol, 3-(dodecylamino)-

HRID 128896Notes

Reaction equation

HRID 128896 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].[CH2:14]1[O:16][CH:15]1[CH2:17][OH:18]>CO>[CH2:1]([NH:13][CH2:14][CH:15]([OH:16])[CH2:17][OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 11164GlycidolHCID 13583Dodecylamine

Product 1

HCID 1024961,2-Propanediol, 3-(dodecylamino)-Yield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

The procedures of Ulsperger et al., J. Prakt. Chemie, Vol. 27, pp. 195-212 (1965), the disclosures of which are hereby incorporated herein by reference in their entirety, were substantially followed. Specifically, 18.54 g laurylamine (0.1M) and 7.4 g glycidol (0.1M) were mixed in 150 ml methanol at 60° C. for 5 hours. The mixture was refluxed for 1 hour at 70° C. The methanol was then removed by rotary evaporation. The product was a solid, 15.3 g (59% yield). After recrystallization from hexane, LDP, was recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.).

Workup

  1. customThe methanol was then removed by rotary evaporation
  2. customAfter recrystallization from hexane, LDP
  3. customwas recovered as a white crystal, m.p. 75°-76° C. (m.p. 76°-76.5° C., lit.)

Sources & evidence

ORD record
ord-c8acc70c0d654e2ea1199cac3948463b
Source dataset
uspto-grants-1995_11
Patent number
US05466438

Reaction notes

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