Glutaric anhydride → 2-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate

HRID 279909

Reaktionsgleichung

Reaktionsgleichung von HRID 279909
[C:1]([O:10][CH2:11][CH:12]([OH:24])[CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:32]1(=[O:39])[O:38][C:36](=[O:37])[CH2:35][CH2:34][CH2:33]1.C([O-])(=O)CCCCCCC>CCOCC.C(Cl)Cl>[C:32]([O:24][CH:12]([CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:39])[CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37]

Komponenten

7

Edukt 4

HCID 7940Glutaric anhydride2×HCID 8471Triethylamine2×HCID 119389OctanoateHCID 1509111,3-Dioctanoyl glycerol

Produkt 1

HCID 233228862-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H)

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureunder reflux until
  3. customThe cooled reaction mixture
  4. washwas washed with 1M hydrochloric acid (2×20 ml.)
  5. dry with materialwith water (2×20 ml.), dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7f45509cc2254f9f8333e2ba5f1b0838
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587262

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