Acetic Acid → HCID 13769239, compound

HRID 2232526Notes

Reaction equation

HRID 2232526 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=[O:25])C>C(O)C>[C:1]1([C:7]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:25])=[O:22])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13769238HCID 13769238, compound

Product 1

HCID 13769239HCID 13769239, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[(2-phenyl-4-quinolyl)oxy]butanol (2.20 g) in glacial aceic acid (10 cc) is added slowly to a solution, cooled to 5° C., of chromic anhydride (2.25 g) in 90% strength acetic acid (5 cc). The temperature is allowed to rise to approximately 20° C., and the mixture is then stirred for one hour at this temperature. Ethanol (50 cc) is then added, the solvents are evaporated off under reduced pressure, the residue is taken up with water (100 cc) and the insoluble material is drained and washed several times with water. This insoluble material is taken up with normal sodium hydroxide solution (15 cc) and heated under reflux for two hours. The insoluble material is removed by filtration and the filtrate acidified by adding glacial acetic acid. The precipitate obtained is drained. 4-[(2-Phenyl-4-quinolyl)oxy]butanoic acid (0.740 g), m.p. 264° C., is obtained.

Workup

  1. customto rise to approximately 20° C.
  2. customthe solvents are evaporated off under reduced pressure
  3. washwashed several times with water
  4. temperatureheated
  5. temperatureunder reflux for two hours
  6. customThe insoluble material is removed by filtration
  7. additionby adding glacial acetic acid
  8. customThe precipitate obtained

Sources & evidence

ORD record
ord-e0f0fba406c445b4ab3ad29d26be897b
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

Loading…