Cyclohexanol → Cyclohexyl Hydrogen Phenylmalonate

HRID 36903

反応式

HRID 36903 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]1(O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 7966CyclohexanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

生成物 1

HCID 19042990Cyclohexyl Hydrogen Phenylmalonate

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 distilled under vacuum. The oily residue was redissolved in dry ether (40 mL), the solution was treated with cyclohexyl alcohol (0.075 mol, 7.9 mL) and refluxed for 2 hours. The mixture was worked up as before to give an oily product which crystallized on standing. Recrystallization was carried out from a benzenepetroleum ether (40°-60°) mixture to give a white crystalline product.

後処理

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. distillationThe clear solution was distilled under vacuum
  3. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  4. temperaturerefluxed for 2 hours
  5. customto give an oily product which
  6. customcrystallized
  7. customRecrystallization
  8. customwas carried out from a benzenepetroleum ether (40°-60°) mixture
  9. customto give a white crystalline product

出典と根拠

ORDレコード
ord-ac0b0d8f6fdf49b792a5870d4b32ad56
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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