Methanol → Ibuprofen methyl ester

HRID 2055725Notes

Reaction equation

HRID 2055725 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].OS(O)(=O)=O.[CH3:21]O>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([O:14][CH3:21])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3672Ibuprofen, (+-)-

Product 1

HCID 109101Ibuprofen methyl ester

Procedure

To a solution of 2-(4-isobutyl-phenyl)-propionic acid (5.00 g, 24.2 mmol) in anhydrous MeOH (150 mL) was added conc H2SO4 (catalytic) and heated to reflux for 5 hrs. After cooling, the solution was evaporated to dryness, the residue dissolved in methylene chloride, dried (MgSO4), filtered and evaporated to yield methyl 2-(4isobutyl-phenyl)-propionate as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.19 (2H, d, J=8,1 Hz), 7.09 (2H, d, J=8.1 Hz), 3.71 (1H, q, J=7.2 Hz), 3.66 (3H, s), 2.44 (2H, d, J=7.2 Hz), 1.84 (1H, app. septet, J=6.7 Hz), 1.48 (3H, d, J=7.2 Hz), 0.90 (6H, d, J=6.6 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hrs
  3. temperatureAfter cooling
  4. customthe solution was evaporated to dryness
  5. dissolutionthe residue dissolved in methylene chloride
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3cd2f5469df94a79997cefe8d8f2ffe8
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

Loading…