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

HRID 2381884Notes

Reaction equation

HRID 2381884 reaction equation
[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]

Participants

4

Reactant 2

HCID 4124402Phosphinic AcidHCID 5364509Methyl Oleate

Product 1

HCID 870660819-{Hydroxy-[1-(7-methoxycarbonyl-heptyl)-decyl]-phosphinoyl}-octadecanoic acid methyl esterYield 95.6%

Reagents, catalysts & solvents 1

HCID 25320Di-tert-amyl peroxideCatalyst

Conditions

Temperature
140 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6b50f44a42674982b71d37573f22bd02
Source dataset
uspto-grants-2012_09
Patent number
US08258253B2

Reaction notes

Loading…