Quinoline → 5-Decenoic acid

HRID 851837

Reaction equation

HRID 851837 reaction equation
Br[CH:2]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=[O:8].N1C2C(=CC=CC=2)C=CC=1.C(OC)(=O)CCCC=CCCCC.C(OC)(=O)CCCCC=CCCC.C(O)(=O)CCCCC=CCCC>>[C:7]([OH:9])(=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 7047QuinolineHCID 22931398Methyl 6-bromodecanoateHCID 53401195Dec-6-enoic acidHCID 53854285HCID 53854285, compoundHCID 54534253Methyl 5-decenoate

Product 1

HCID 534008795-Decenoic acidYield 35%

Procedure

Methyl 6-bromodecanoate (1.2 g) and quinoline (1.2g) were mixed together, and then allowed to react at 240° C. for 5 minutes. After the reaction was completed, the reaction solution was extracted with ether, washed with dilute sulfuric acid, washed with water, dried, evaporated to remove the solvent, and then distilled, thereby giving a mixture of methyl 5-decenoate and methyl 6-decenoate (310 mg). The mixture was hydrolyzed in a coventional manner, thereby giving a mixture (270 mg) of 5-decenoic acid and 6-decenoic acid (1/1).

Workup

  1. customto react at 240° C. for 5 minutes
  2. extractionthe reaction solution was extracted with ether
  3. washwashed with dilute sulfuric acid
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. distillationdistilled
  9. customgiving

Sources & evidence

ORD record
ord-8dd77bdcdc434d79a2d242b7afbf50d2
Source dataset
uspto-grants-2007_08
Patent number
US07252849B2

Linked notes

Loading…