4-Chlorophenol → Diethyl 2-(4-chlorophenoxy)malonate

HRID 327654

Reaction equation

HRID 327654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:20])[CH:13](Cl)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:11][C:12](=[O:20])[CH:13]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 84182Diethyl chloromalonate

Product 1

HCID 18402089Diethyl 2-(4-chlorophenoxy)malonateYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 38.6 g (0.3 mole) of 4-chlorophenol, 70 g (0.36 mole) of diethylchloromalonate and 69.1 g (0.5 mole) of anhydrous potassium carbonate in 750 ml of acetone was heated at reflux for 48 hr, cooled, filtered and the filtrate concentrated. The residue was diluted with 250 ml of ethyl ether and was washed successively with two 100 ml portions of a 1% NaOH solution, once with H2O and once with brine, dried (sodium sulfate) and concentrated to give an oil which gradually crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and dried to yield 72.6 g (84%) of white solid. An analytical sample, mp 43.5°-45° C. (lit. mp 58°-60° C.), was recrystallized from petroleum ether (60°-110° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hr
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. additionThe residue was diluted with 250 ml of ethyl ether
  7. washwas washed successively with two 100 ml portions of a 1% NaOH solution, once with H2O and once with brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated
  10. customto give an oil which
  11. customgradually crystallized
  12. customThe solid was triturated with petroleum ether (30°-60° C.)
  13. filtrationcollected by filtration
  14. customdried

Sources & evidence

ORD record
ord-dd00681a2d144f139f6491d84de06075
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Linked notes

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