Formic Acid → HCID 23466089, compound

HRID 1701593Notes

Reaction equation

[CH2:1]([O:17][CH2:18][CH:19]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[O:20][CH2:21][CH2:22]C#N)[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][CH3:16].Cl.[CH:44]([OH:46])=[O:45]>>[CH2:1]([O:17][CH2:18][CH:19]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[O:20][CH2:21][CH2:22][C:44]([OH:46])=[O:45])[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][CH3:16]

Participants

Reactant 3

HCID 284Formic Acid

HCID 313Hydrochloric Acid

HCID 23466163HCID 23466163, compound

Product 1

HCID 23466089HCID 23466089, compoundYield 71%

Procedure

A mixture of 1,3-di-O-(n-hexadecyl)-2-O-(2-cyanoethyl)-glycerol (4.8 g., 8.1 mmoles), concentrated hydrochloric acid (50 ml.) and formic acid (50 ml.) was stirred for 16 hours at reflux, then cooled and extracted with ether (3×100 ml.). The combined ether extract was washed with water (200 ml.), dried (MgSO4), filtered and evaporated in vacuo to yield 1,3-di-O-(n-hexadecyl)-2-O-(2-carboxyethyl)-glycerol solids (4.5 g.), which were purified by silica gel chromatography (elution with toluene:ethanol) [3.5 g., 71% yield, m.p. 43°-45° C., ir (CHCl3) 1740 cm-1, n.m.r. (CDCl3) δ 3.93 (t, J=6 Hz, 2, --OCH2CH2COOH) and 2.65 (t, J=6 Hz, 2, --OCH2CH2COOH)].

Workup

temperatureat reflux
temperaturecooled
extractionextracted with ether (3×100 ml.)
extractionThe combined ether extract
washwas washed with water (200 ml.)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-da11e6420f9e464aa16c73f18199de72
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04193999

Reaction notes

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