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

HRID 127014Notes

Reaction equation

HRID 127014 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-f473556008f04e2dbf8d458f532c78a2
Source dataset
uspto-grants-1981_03
Patent number
US04254274

Reaction notes

Loading…