Acetovanillone → 1-[4-[(5-Chloropentyl)oxy]-3-methoxyphenyl]ethanone

HRID 1709828Notes

Reaction equation

HRID 1709828 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][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:19][CH2:18][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 960701-Bromo-5-chloropentane

Product 1

HCID 144071771-[4-[(5-Chloropentyl)oxy]-3-methoxyphenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 59.7 g (0.36 mole) of acetovanillone, 100 g (0.539 mole) of 1-bromo-5-chloropentane and 138 g (1 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 20 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which crystallized in petroleum ether (30°-60° C.). The solid was collected by filtration, washed with petroleum ether and dried to yield 81.4 g (84%) of fluffy, white solid. The solid was recrystallized from isopropyl ether, m.p. 57°-58° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oil which
  6. customcrystallized in petroleum ether (30°-60° C.)
  7. filtrationThe solid was collected by filtration
  8. washwashed with petroleum ether
  9. customdried
  10. customto yield 81.4 g (84%) of fluffy, white solid
  11. customThe solid was recrystallized from isopropyl ether, m.p. 57°-58° C.

Sources & evidence

ORD record
ord-1090269fd3ad4fde8bbd52c54e07f0b0
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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