Hydrogen Bromide → Loxoprofen

HRID 971863Notes

Reaction equation

HRID 971863 reaction equation
C(OC([C:6]1([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:25])[C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=2)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])=O)C.Br>O1CCOCC1>[O:11]=[C:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH3:25])[C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 11131780Ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate

Product 1

HCID 3965LoxoprofenYield 92.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Twenty grams of ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate was dissolved in 30 ml of dioxane and 100 ml of 47% hydrobromic acid and the solution was refluxed for 6 hours. The reaction mixture was then extracted with ether, the extract was washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give an yellow oily substance. The product was subjected to a vacuum distillation to yield 13.1 g of the desired compound as a colorless oily substance, b.p. 190°-195° C. at 0.3 mm Hg (bath temp.). The compound solidified as it was cooled to crystals, m.p. 108.5°-111° C.

Workup

  1. extractionThe reaction mixture was then extracted with ether
  2. washthe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent removed by distillation
  5. customto give an yellow oily substance
  6. distillationThe product was subjected to a vacuum distillation

Sources & evidence

ORD record
ord-5f3e63895a354164abacd678bc28a08d
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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