Hydrogen Bromide → 4-(2-Oxo-1-cyclopentylidenemethyl)phenylacetic acid

HRID 1902759Notes

Reaction equation

HRID 1902759 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]([CH2:14][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]([CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 54231923Ethyl 4-(2-oxo-1-cyclopentylidenemethyl)phenylacetate

Product 1

HCID 541547854-(2-Oxo-1-cyclopentylidenemethyl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.4 g of ethyl 4-(2-oxo-1-cyclopentylidenemethyl)phenylacetate in 100 ml of a 10% aqueous solution of hydrobromic acid and 10 ml of dioxane was heated under reflux for 1 hour. After cooling, the reaction mixture was extracted with ether, an ether layer was washed with water and dried. The ether was distilled off and the residual oily substance was distilled under reduced pressure to give 0.1 g of an oily substance having a boiling point of 205°-210° C./0.25 mmHg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ether
  5. washan ether layer was washed with water
  6. customdried
  7. distillationThe ether was distilled off
  8. distillationthe residual oily substance was distilled under reduced pressure
  9. customto give 0.1 g of an oily substance

Sources & evidence

ORD record
ord-92f1a69b01de4300bd525b2238f39689
Source dataset
uspto-grants-1982_12
Patent number
US04365076

Reaction notes

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