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

HRID 327654

反応式

HRID 327654 の反応式
[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]

参加物

5

反応物 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 84182Diethyl chloromalonate

生成物 1

HCID 18402089Diethyl 2-(4-chlorophenoxy)malonate収率 84.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-dd00681a2d144f139f6491d84de06075
出典データセット
uspto-grants-1993_12
特許番号
US05273993

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