1-Bromo-3-chloropropane → HCID 14407178, compound

HRID 346238

Reaction equation

HRID 346238 reaction equation
[C:1]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:1](=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([O:9][CH2:17][CH2:18][CH2:19][Cl:20])=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

Product 1

HCID 14407178HCID 14407178, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 g (0.238 mole of ethyl homovanillate (98% Aldrich), 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 L of acetone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30°-60°) to yield 44.4 g (65%) of title compound a white solid, mp 36°-38° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oil which
  6. customgradually crystallized to a semi-solid
  7. customThe solid was recrystallized from ethyl ether-petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-21d125186760420e8eb498b177e62f40
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Linked notes

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