Acetic Acid → HCID 18001066, compound

HRID 1870437Notes

Reaction equation

HRID 1870437 reaction equation
Cl.[C:2]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15]CC(C)(C)N=3)=[C:10]([CH2:21][CH2:22][CH3:23])[CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:26])C>>[C:2]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:15])=[O:26])=[C:10]([CH2:21][CH2:22][CH3:23])[CH:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18001067HCID 18001067, compound

Product 1

HCID 18001066HCID 18001066, compound

Procedure

To a mixture of conc. hydrochloric acid (30 ml) and glacial acetic acid (10 ml) is added 2-(4-phenyl-2-n-propylphenyl)-4,4-dimethyl-2-oxazoline (2.70 g), and the mixture is refluxed for three days (nine hours×3). The reaction solution is concentrated to about half volume thereof under reduced pressure, and cooled over an ice-bath. The precipitated crystals are collected by filtration, and purified by silica gel column chromatography (solvent; dichloromethane→dichloromethane:methanol=50:1). The desired fractions are combined, evaporated to remove the solvent, and the crystalline residue is recrystallized from n-hexane to give 4-phenyl-2-n-propylbenzoic acid (1.67 g) as colorless needles.

Workup

  1. temperaturethe mixture is refluxed for three days (nine hours×3)
  2. concentrationThe reaction solution is concentrated to about half volume
  3. temperatureunder reduced pressure, and cooled over an ice-bath
  4. filtrationThe precipitated crystals are collected by filtration
  5. custompurified by silica gel column chromatography (solvent; dichloromethane→dichloromethane:methanol=50:1)
  6. customevaporated
  7. customto remove the solvent
  8. customthe crystalline residue is recrystallized from n-hexane

Sources & evidence

ORD record
ord-3d5176e01b1a4baa8c134c5bb4bc38de
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

Loading…