Hydrochloric Acid → N-hydroxymethyl-n-octadecenyl succinimide

HRID 2285873Notes

Reaction equation

[CH:1]([CH:19]1[CH2:24][C:23](=[O:25])[NH:22][C:20]1=[O:21])=[CH: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][CH2:16][CH2:17][CH3:18].C=O.[C:28](=O)(O)[O-:29].[Na+].Cl>O.CCCCCCC>[OH:29][CH2:28][N:22]1[C:23](=[O:25])[CH2:24][CH:19]([CH:1]=[CH: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][CH2:16][CH2:17][CH3:18])[C:20]1=[O:21]

Participants

Conditions

Temperature: 70 °C

Procedure

In a reaction vessel was placed 1 liter of heptane and 550 gms of octadecenyl succinimide. The mixture was heated to 70° C. with stirring and a mixture of 137 gms of 36% aqueous formaldehyde and 22 gms of sodium bicarbonate was added. This mixture was stirred at reflux for 4 hours. Then 300 ml of water was added and the mixture neutralized with hydrochloric acid. The aqueous layer was separated and removed, then 500 ml butanol was added to the organic layer and the mixture washed with hot water. The organic layer was separated and heptane, butanol and residual water distilled off leaving as the product N-hydroxymethyl-n-octadecenyl succinimide.

Workup

customIn a reaction vessel was placed
additionwas added
stirringThis mixture was stirred
temperatureat reflux for 4 hours
customThe aqueous layer was separated
customremoved
addition500 ml butanol was added to the organic layer
washthe mixture washed with hot water
customThe organic layer was separated
distillationheptane, butanol and residual water distilled off

Sources & evidence

ORD record: ord-9ff61b37fc12427d8dc2e9b374324cc8
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04325827

Reaction notes

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