Isopropanol → Isopropyl Hydrogen Phenylmalonate

HRID 36902

反応式

HRID 36902 の反応式
[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH:18](O)([CH3:20])[CH3:19]>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH:18]([CH3:20])[CH3:19])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

生成物 1

HCID 19042994Isopropyl Hydrogen Phenylmalonate収率 60%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 3283Diethyl Ether溶媒

実験手順

Phenylmalonic acid (13.5 g, 0.07 mol ) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was evaporated under reduced pressure to remove any residual thionyl chloride. The oily residue was redissolved in dry ether (40 mL), and the solution was treated with isopropyl alcohol (0.075 mol, 5.76 mL), refluxed for 2 hours and worked up as before to give the titled compound.

後処理

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. customThe clear solution was evaporated under reduced pressure
  3. customto remove any residual thionyl chloride
  4. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  5. temperaturerefluxed for 2 hours

出典と根拠

ORDレコード
ord-af73ff0456864c18a081b75ef0069f5f
出典データセット
uspto-grants-1995_05
特許番号
US05418244

関連ノート

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