Ibuprofen, (+-)- → Phthalidyl 2-(4-isobutylphenyl)propionate

HRID 371108Notes

Reaction equation

HRID 371108 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].Br[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:19](=[O:20])[O:18]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([O:14][CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19](=[O:20])[O:18]2)=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 3672Ibuprofen, (+-)-HCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 12769702Phthalidyl 2-(4-isobutylphenyl)propionateYield 82.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 6.2 g of 2-(4-isobutylphenyl)propionic acid in 30 ml of chloroform and 3.4 g of triethylamine, a solution of 6.2 g of 3-bromophthalide in 20 ml of chloroform is added. The solution thus obtained is stirred 24 hours at room temperature (about +22° C.), the organic phase is washed with an aqueous solution of sodium bicarbonate, then with water and finally it is dried on anhydrous sodium sulfate and evaporated to dryness. The residue, crystallized from petroleum ether, yields 8.1 g of phthalidyl 2-(4-isobutylphenyl)propionate; m.p. 62°-65° C. IR: 1795 and 1780 cm1

Workup

  1. customThe solution thus obtained
  2. washthe organic phase is washed with an aqueous solution of sodium bicarbonate
  3. dry with materialwith water and finally it is dried on anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue, crystallized from petroleum ether

Sources & evidence

ORD record
ord-becd6a5b7db84e83858dbfd9caf14c78
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Reaction notes

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