Cyclohexanol → Cyclohexyl Hydrogen Phenylmalonate

HRID 53198

반응식

HRID 53198 반응식
[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

참가 물질

6

반응물 3

HCID 7966CyclohexanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

생성물 1

HCID 19042990Cyclohexyl Hydrogen Phenylmalonate

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 3283Diethyl Ether용매

실험 절차

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 benzene-petroleum ether (40°-60°) mixture to give a white crystalline product.

후처리

  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 benzene-petroleum ether (40°-60°) mixture
  9. customto give a white crystalline product

출처 및 근거

ORD 기록
ord-4f01c620be9f4001a84e5ba6c5b4be16
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618826

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