2-Acetylhydroquinone → 5'-(6-Chlorohexoxy)-2'-hydroxyacetophenone

HRID 1197954Notes

Reaction equation

HRID 1197954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 11430Potassium CarbonateHCID 805161-Bromo-6-chlorohexane

Product 1

HCID 149830945'-(6-Chlorohexoxy)-2'-hydroxyacetophenoneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2',5'-dihydroxyacetophenone (150 g), 1-bromo-6-chlorohexane (186 g), and potassium carbonate (186 g) in 2500 mL of 2-butanone was refluxed for 16 hours. The solvent was removed in vacuo and the residue was stirred with 1000 mL of methylene chloride. After filtration, the filtrate was washed with 10% KOH (250 mL), water (250 mL), and brine (250 mL). The solution was dried over magnesium sulfate and the solvent was removed to give an oil which solidified overnight to give 210 g of 5'-(6-chlorohexoxy)-2'-hydroxyacetophenone as a yellow solid.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was removed in vacuo
  3. filtrationAfter filtration
  4. washthe filtrate was washed with 10% KOH (250 mL), water (250 mL), and brine (250 mL)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was removed
  7. customto give an oil which

Sources & evidence

ORD record
ord-f7f8e4718e504fa38ffa85efeeafa1f2
Source dataset
uspto-grants-1994_01
Patent number
US05278174

Reaction notes

Loading…