1-Bromo-3-chloropropane → HCID 15020344, compound

HRID 1460229Notes

Reaction equation

HRID 1460229 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([O:15][CH3:16])[CH:9]=1)=[O:7])(=[O:3])[CH3:2].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:18][CH2:19][CH2:20][Cl:21])=[C:10]([O:15][CH3:16])[CH:9]=1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 15020343HCID 15020343, compound

Product 1

HCID 15020344HCID 15020344, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 31.5 g (0.14 mol) of 2-(acetyloxy)-1-(4-hydroxy-3-methoxyphenyl)ethanone, 44.1 g (0.28 mole) of 1-bromo-3-chloropropane and 58 g (0.42 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 16 hr. The mixture was cooled, filtered, and the filtrate concentrated to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and dried to yield 38.7 g (92%) of title compound as a pale-yellow solid. An analytical sample, mp 93°-96° C., was prepared from 2-propanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give a solid residue
  7. customThe solid was triturated with petroleum ether (30°-60° C.)
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-d6c94be6edcd405b8aa7bce7f806e123
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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