Ketoprofen → Phthalidyl 2-(3-benzoylphenyl)propionate

HRID 371111

Reaction equation

HRID 371111 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1>C(Cl)(Cl)Cl>[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([O:18][CH:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30](=[O:31])[O:29]2)=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3825KetoprofenHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 12769703Phthalidyl 2-(3-benzoylphenyl)propionateYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 7.6 g of 2-(3-benzoylphenyl)propionic acid in 30 ml of chloroform and 3.4 g of triethylamine is added a solution of 6.2 g of 3-bromophthalide in 20 ml of chloroform. The solution thus obtained is stirred 25 hours at room temperature, the organic phase is washed with an aqueous solution of sodium bicarbonate, then with water and finally dried on anhydrous sodium sulfate and evaporated to dryness to give the phthalidyl 2-(3-benzoylphenyl)propionate; yield 79%.

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 dried on anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-13e304f3ba35400987a80225de0e105e
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Linked notes

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