Hydrogen Bromide → 4-[(2-Oxocyclopentyl)methyl]benzeneacetic acid

HRID 971864Notes

Reaction equation

HRID 971864 reaction equation
Br.C(OC([C:7]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=2)[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])=O)C>O1CCOCC1>[O:12]=[C:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 53942620HCID 53942620, compound

Product 1

HCID 199226184-[(2-Oxocyclopentyl)methyl]benzeneacetic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a mixture of 20 ml of 47% hydrobromic acid and 15 ml of dioxane was dissolved 9.2 g of ethyl 4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenylacetate and the solution was refluxed for 6 hours. The solvent was then removed by distillation from the reaction mixture, the residue was poured into ice-water and extracted with ether. The extract was washed with water, dried over anhydrous sodium sulfate, the solvent removed by distillation to give an oily substance, which was subjected to a vacuum distillation to yield 6.0 g of an oily product, b.p. 185°-195° C. at 0.7 mm Hg (bath temp.).

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. customThe solvent was then removed by distillation from the reaction mixture
  3. additionthe residue was poured into ice-water
  4. extractionextracted with ether
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent removed by distillation
  8. customto give an oily substance, which
  9. distillationwas subjected to a vacuum distillation

Sources & evidence

ORD record
ord-c243ccd4942943939d5b886bce7bfe8f
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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