Sodium Carbonate → N,N-didodecylglycine linalyl ester
Reaction equation
Cl[CH2:2][C:3]([O:5][C:6]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])([CH:8]=[CH2:9])[CH3:7])=[O:4].[CH2:16]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])([CH:8]=[CH2:9])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Linalyl chloroacetate (5.77 g, 25 mmol, 1 eq), in toluene (50 ml), was slowly added to didodecylamine (10 g, 28.3 mmol, 1.13 eq) and sodium carbonate (5.3 g, 0.05 mol, 2 eq), in toluene (50 ml). The reaction mixture was stirred at 60° C. for two weeks after which the reaction seemed completed by 1H NMR. The sodium carbonate was filtered off, the filtrate was concentrated under vacuum and diethyl ether (200 ml) was added before storage of the solution at 4° C. for 12 hours. Then, the solution was filtered and removal of ether under vacuum yielded to the expected N,N-didodecylglycine linalyl ester as a yellow oil.
Workup
- filtrationThe sodium carbonate was filtered off
- concentrationthe filtrate was concentrated under vacuum and diethyl ether (200 ml)
- additionwas added before storage of the solution at 4° C. for 12 hours
- filtrationThen, the solution was filtered
- customremoval of ether under vacuum
Sources & evidence
- ORD record
- ord-e4d77fb9cd0f4f1b93f13f11d2dd003d
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958870
Reaction notes
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