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Sodium Carbonate → N,N-didodecylglycine linalyl ester

HRID 619009
Notes
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Reaction equation

HRID 619009 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 18157DidodecylamineHCID 231030Linalyl chloroacetate

Product 1

HCID 21845415N,N-didodecylglycine linalyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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

  1. filtrationThe sodium carbonate was filtered off
  2. concentrationthe filtrate was concentrated under vacuum and diethyl ether (200 ml)
  3. additionwas added before storage of the solution at 4° C. for 12 hours
  4. filtrationThen, the solution was filtered
  5. customremoval of ether under vacuum

Sources & evidence

ORD record
ord-e4d77fb9cd0f4f1b93f13f11d2dd003d
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958870

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes