Dioctadecylamine → [2-(Dioctadecylamino)-2-oxoethoxy]acetic acid

HRID 1246733Notes

Reaction equation

HRID 1246733 reaction equation
[CH2:1]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:38]1(=[O:45])[O:44][C:42](=[O:43])[CH2:41][O:40][CH2:39]1>C1(C)C=CC=CC=1>[N:19]([C:42]([CH2:41][O:40][CH2:39][C:38]([OH:45])=[O:44])=[O:43])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 66989DioctadecylamineHCID 782321,4-Dioxane-2,6-dione

Product 1

HCID 18689621[2-(Dioctadecylamino)-2-oxoethoxy]acetic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of dioctadecylamine (2.0 g, 3.8 mmol) and diglycolic anhydride (0.44 g, 3.8 mmol) was refluxed in toluene (50 mL) for 48 h. The solvent was then evaporated and the crude product recrystallized form CHCl3 to give (C18H37)2NCOCH2OCH2COOH as a white solid (2.12 g, 87%), mp 80–81° C. 1H-NMR (300 MHz, δ, CDCl3): 0.87 (6H, t, J=6.9 Hz), 1.25 (64H, m), 1.55 (4H, bs), 3.07 (2H, t, J=7.8 Hz), 3.34 (2H, t, J=7.8 Hz), 4.21 (2H, s), 4.38 (2H, s). 13C-NMR (75 MHz, δ, CDCl3): 14.2, 22.8, 26.9, 27.0, 27.5, 28.7, 29.4, 29.5, 29.6, 29.7, 29.8, 32.0, 47.0, 71.4, 73.2, 171.0, 172.2. IR (KBr, cm−1): 1748 (CO), 1602 (CO).

Workup

  1. customThe solvent was then evaporated
  2. customthe crude product recrystallized
  3. customform CHCl3

Sources & evidence

ORD record
ord-c30c7237ac7d43379cfbddac5bc4cc9e
Source dataset
uspto-grants-2006_10
Patent number
US07129208B2

Reaction notes

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