Phosphinic Acid → 9-{Hydroxy-[1-(7-methoxycarbonyl-heptyl)-decyl]-phosphinoyl}-octadecanoic acid methyl ester

HRID 1661853

Reaktionsgleichung

Reaktionsgleichung von HRID 1661853
[PH2:1]([OH:3])=[O:2].[C:4]([O:23][CH3:24])(=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(OOC(CC)(C)C)(CC)(C)C>[CH3:24][O:23][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([P:1]([OH:3])([CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:23][CH3:24])=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

4

Edukt 2

HCID 4124402Phosphinic AcidHCID 5364509Methyl Oleate

Produkt 1

HCID 870660819-{Hydroxy-[1-(7-methoxycarbonyl-heptyl)-decyl]-phosphinoyl}-octadecanoic acid methyl esterAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25320Di-tert-amyl peroxideKatalysator

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3.1 mL (0.03 moles) of 50% aqueous hypophosphorous acid and 16.92 g (0.06 moles) of methyl oleate (CE-1897 from P&G Chemical; iodine value=90) are mixed in a 100 mL single neck flask equipped with a distillation head. The mixture is purged with argon to remove oxygen and is heated under argon at 140° C. to remove water. After water is removed the mixture is cooled and 0.5 mL (0.0023 moles) of di-tert-amylperoxide are added and the mixture is purged with argon to remove oxygen and is heated under argon for 5 hours at 140° C. Tert-amyl alcohol is removed by distillation and 18.9 g (quantitative yield) of 9-{hydroxy-[1-(7-methoxycarbonyl-heptyl)-decyl]-phosphinoyl}-octadecanoic acid methyl ester (mixture of isomers) is obtained as a colorless wax melting near ambient temperature.

Aufarbeitung

  1. customequipped with a distillation head
  2. customThe mixture is purged with argon
  3. customto remove oxygen
  4. customto remove water
  5. customAfter water is removed the mixture
  6. temperatureis cooled
  7. customthe mixture is purged with argon
  8. customto remove oxygen
  9. temperatureis heated under argon for 5 hours at 140° C
  10. customTert-amyl alcohol is removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-9bef98b036e14e2da94fb091a983d15d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030435B2

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