Acetovanillone → HCID 23036409, compound

HRID 1709850Notes

Reaction equation

HRID 1709850 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].Br[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][O:10][C:9]1[CH:11]=[CH:12][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:7][CH3:8]

Participants

5

Reactant 3

HCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 23036409HCID 23036409, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 16.6 g (0.1 mole) of acetovanillone, 34.3 g (0.2 mole) of 1-bromo-4-chlorobutane and 41.4 g (0.3 mole) of anhydrous potassium carbonate in 500 ml of acetone was heated at reflux for 18 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to give an oil which readily crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and dried to yield 24.4 g (95%) of title compound as an off-white solid. An analytical sample, mp 68.5°-70.5° C., was prepared from isopropyl ether.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give an oil which
  7. customreadily crystallized
  8. customThe solid was triturated with petroleum ether (30°-60° C.)
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-499c3a23f7174b0b821db4c42310334a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…