Hydrogen Bromide → 2-(4-((2-Oxocyclopentylidene)methyl)phenyl)propanoic acid

HRID 127010Notes

Reaction equation

HRID 127010 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1.Br>O1CCOCC1>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 53946190Ethyl 2-[4-(2-oxo-1-cyclopentylidenemethyl)phenyl]propionate

Product 1

HCID 540467252-(4-((2-Oxocyclopentylidene)methyl)phenyl)propanoic acidYield 23.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.4 g of ethyl 2-[4-(2-oxo-1-cyclopentylidenemethyl)phenyl]propionate in 15 ml of dioxane and 100 ml of a 10% aqueous solution of hydrogen bromide was heated under reflux for 1 hour. After cooling, the reaction mixture was extracted with ether. The extract was washed with water and dried over anhydrous sodium sulfate. The ether was distilled off to leave an oily substance, which was then vacuum distilled to afford 0.3 g of the desired product having a boiling point of 210°-215° C./0.2 mmHg (bath temp.). This product solidified and crystallized after cooling. m.p. 106°-107° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe ether was distilled off
  7. customto leave an oily substance, which
  8. distillationvacuum distilled

Sources & evidence

ORD record
ord-7471a38af4d04b908ade7478567a3151
Source dataset
uspto-grants-1981_03
Patent number
US04254274

Reaction notes

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