Succinic anhydride → HCID 86592293, compound

HRID 645332Notes

Reaction equation

HRID 645332 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1.C1C[O:30]CC1>>[C:20]([OH:25])(=[O:26])[CH2:21][CH2:22][C:23]([OH:30])=[O:24].[CH2:1]([NH-:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 8028TetrahydrofuranHCID 5356789Oleylamine

Product 1

HCID 86592293HCID 86592293, compound

Conditions

Temperature
68 °C

Procedure

Oleyl amide succinic acid was synthesised using the following procedure. To a solution of 50 of oleyl amine in 100 ml THF was added 22 g, that is to say 1.2 mole equivalents, of succinic anhydride. The solution was then refluxed at a temperature of 68° C. for 48 hours to ensure the complete reaction shown in the FIG. 12. THF was removed under vacuum and 50 ml of petroleum ether was added. The excess succinic anhydride not soluble in petroleum ether was removed by filtration on Whatman paper 43. The petroleum ether solution was cooled down and maintained at −10° C. overnight using a refrigerated centrifuge. The white solid was then collected by centrifuging for 30 min at 9000 rpm. The product was washed with cold petroleum ether and dried under vacuum.

Workup

  1. customthe complete reaction
  2. customTHF was removed under vacuum and 50 ml of petroleum ether
  3. additionwas added
  4. customThe excess succinic anhydride not soluble in petroleum ether was removed by filtration on Whatman paper 43
  5. temperatureThe petroleum ether solution was cooled down
  6. temperaturemaintained at −10° C. overnight
  7. customThe white solid was then collected by centrifuging for 30 min at 9000 rpm
  8. washThe product was washed with cold petroleum ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-d2a096cc1cdc4daf92fdd3211e7dc840
Source dataset
uspto-grants-2010_04
Patent number
US07704926B2

Reaction notes

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