Quinoline → Ethyl octadecyl fumarate

HRID 232119Notes

Reaction equation

HRID 232119 reaction equation
[CH2:1]([OH:19])[CH2:2][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].N1C2C(=CC=CC=2)C=CC=1.[Cl-].[CH2:31]([O:33][C:34](=[O:40])/[CH:35]=[CH:36]/[C:37](O)=[O:38])[CH3:32]>C(O)C>[C:34]([O:33][CH2:31][CH3:32])(=[O:40])/[CH:35]=[CH:36]/[C:37]([O:19][CH2:1][CH2:2][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])=[O:38]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 8221Stearyl AlcoholHCID 86609896Fumaric acid monoethylester monochloride

Product 1

HCID 14014469Ethyl octadecyl fumarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

135 g (0.5 mole) of 1-octadecanol and 65 ml (0.55 mole) of quinoline are dissolved, with stirring, at 40° C. in 500 ml of ethanol-free chloroform. Over the course of one hour, 89.4 g (0.55 mole) of fumaric acid monoethylesterchloride were added drop by drop to the clear solution and it was boiled for 2 hours under reflux. The reaction mixture was diluted with 500 ml of petroleum ether and extracted twice with 0.5N hydrochloric acid, water, 5% potassium carbonate solution and water, dried over sodium sulfate and concentrated under reduced pressure. The solid residue was recrystallized from 95% ethanol. Yield: 139 g of product having a melting point of 42° C.

Workup

  1. temperatureunder reflux
  2. extractionextracted twice with 0.5N hydrochloric acid, water, 5% potassium carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-2d19b1bdbb4d4153bcdc2cdc2d62cb66
Source dataset
uspto-grants-1989_07
Patent number
US04851439

Reaction notes

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