Palmitoyl chloride → HCID 21711987, compound

HRID 650454Notes

Reaction equation

HRID 650454 reaction equation
[OH: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][C:17]([O:19][CH2:20][O:21][C:22](=[O:39])[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][CH2:37][OH:38])=[O:18].[C:40](Cl)(=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C(OCC)C>[C:40]([O: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][C:17]([O:19][CH2:20][O:21][C:22](=[O:39])[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][CH2:37][O:38][C:2](=[O:1])[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][CH3:17])=[O:18])(=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 21711985HCID 21711985, compound

Product 1

HCID 21711987HCID 21711987, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methylene bis(16-hydroxyhexadecanoate) (1.0 mmol) and palmitoyl chloride (7.0 mmol) was refluxed in diethyl ether (10 ml) for 24 hours before the solvent was evaporated. The residual material was purified on a silica gel flash column eluting first with hexane/chloroform (2:1) and then with chloroform. Yield 88%, white solid. 1H NMR (CDCl3): δ 0.88 (6 H, t, J 6.7 Hz), 1.2-1.4 (92 H, m), 1.5-1.7 (12 H, m), 2.28 (4 H, t, J 7.5 Hz), 2.35 (4 H, t, J 7.6 Hz), 4.05 (4 H, t, J 6.7 Hz), 5.75 (2 H, s). 13C NMR (CDCl3): δ 14.11, 22.70, 24.64, 25.06, 25.97, 28.70, 29.04, 29.19, 29.25, 29.29, 29.38, 29.47, 29.50, 29.56, 29.62, 29.67, 29.70, 29.71, 31.94, 34.00, 34.43, 64.39, 79.06, 172.59, 173.97.

Workup

  1. customwas evaporated
  2. customThe residual material was purified on a silica gel flash column
  3. washeluting first with hexane/chloroform (2:1)

Sources & evidence

ORD record
ord-812bd5ee1be14dfb80babe9600fed8a2
Source dataset
uspto-grants-2001_08
Patent number
US06274120B1

Reaction notes

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