Water → Ibuprofen Piconol

HRID 26455

Reaction equation

HRID 26455 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20](Cl)=[O:21])=[CH:15][CH:14]=1)[CH:10]([CH3:12])[CH3:11].C(N(CC)CC)C.O>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:20](=[O:21])[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:14][CH:15]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11474PiconolHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Product 1

HCID 3673Ibuprofen PiconolYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.2 g of 2-pyridinemethanol in 20 ml of tetrahydrofuran were added 3 g of 2-(4-isobutylphenyl)propionic acid chloride and subsequently 2.7 g of triethylamine, and the mixture was reacted at room temperature for 2 hours. After the reaction was complete, the crystals produced were removed by filtration. The filtrate was freed of solvent by distillation to leave a residue, to which was added water. The resulting mixture was extracted with ether. The ether extract was dehydrated and freed of ether by distillation. The oily residue thus obtained was distilled in vacuo to give 3.5 g of 2-(4-isobutylphenyl)propionic acid-2-pyridylmethyl ester as a pale yellow oil, boiling at 138°-140° C./0.15 mmHg. Mass spectrum: parent ion 297 m/e.

Workup

  1. customthe mixture was reacted at room temperature for 2 hours
  2. customthe crystals produced
  3. customwere removed by filtration
  4. distillationThe filtrate was freed of solvent by distillation
  5. customto leave a residue
  6. extractionThe resulting mixture was extracted with ether
  7. extractionThe ether extract
  8. distillationfreed of ether by distillation
  9. customThe oily residue thus obtained
  10. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-54cc47a78449481494b15c343d1d17db
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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