Ethanol → Dodecyl N,N-dimethylalaninate

HRID 2227563Notes

Reaction equation

HRID 2227563 reaction equation
[CH3:1][N:2]([CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].[CH2:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CC.C[O-].[Na+].C(O)C>C1(C)C=CC=CC=1>[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:9][CH2:8][O:7][C:5]([CH:4]([N:2]([CH3:3])[CH3:1])[CH3:10])=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 81931-DodecanolHCID 10942334Sodium MethoxideHCID 13010786HCID 13010786, compound2×

Product 1

HCID 3025823Dodecyl N,N-dimethylalaninate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DDAIP was prepared by transesterification of ethyl 2-(N,N-dimethylamino)-propionate obtained from Varsal Instruments Inc. (Warminster, Pa.). Specifically, a mixture ethyl 2-(N,N-dimethylamino)-propionate, 1-dodecanol, and sodium methoxide predissolved in toluene was refluxed for about 2 hours. As ethanol formed, it was removed by azeotropic distillation. After about 2 hours of refluxing, the remaining reaction product was filtered to remove solids.

Workup

  1. temperaturewas refluxed for about 2 hours
  2. customit was removed by azeotropic distillation
  3. temperatureAfter about 2 hours of refluxing
  4. customthe remaining reaction product
  5. filtrationwas filtered
  6. customto remove solids

Sources & evidence

ORD record
ord-19c73369a2e24b6394f152a54b63f3ef
Source dataset
uspto-grants-2002_07
Patent number
US06414028B1

Reaction notes

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