반응 #1746

ord-989f1c45e316471198b7f2d873102bdb

반응 방정식

ClCCl
methylene chloride
CC(=O)OC1CCC(c2ccccc2)CC1
O-acetyl-4-phenylcyclohexanol
C=O
paraformaldehyde
Cl
Hydrogen chloride
CC(=O)O[C@H]1CC[C@H](c2ccc(CCl)cc2)CC1
trans-O-Acetyl-4-(4-chloromethylphenyl)-cyclohexanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타rises to about 30° C.
  2. 2
    기타a substantially homogeneous solution is formed
  3. 3
    기타to react for 15 hours at ambient temperature
  4. 4
    기타The organic phase is separated off
  5. 5
    추출the aqueous phase is extracted with methylene chloride again
  6. 6
    세척They are washed until neutral,
  7. 7
    기타dried
  8. 8
    기타evaporated in vacuo
  9. 9
    기타The yellow oil remaining is crystallised by trituration with diisopropylether
  10. 10
    기타the solid product is recrystallised from diisopropylether
  11. 11
    기타White crystals are obtained

실험 절차

A solution of 24.3 g (0.11 mol) of O-acetyl-4-phenylcyclohexanol in 1300 ml of methylene chloride is combined with 26.0 g (0.86 mol) of paraformaldehyde and 26.0 g (0.19 mol) of zinc chloride. Hydrogen chloride is introduced into this suspension, with stirring, for 2.5 hours, whilst the temperature rises to about 30° C. and a substantially homogeneous solution is formed. The mixture is then allowed to react for 15 hours at ambient temperature and the reaction mixture is then hydrolysed with stirring in about 1.5 litres of ice water. The organic phase is separated off, the aqueous phase is extracted with methylene chloride again and the two organic phases are combined. They are washed until neutral, dried and evaporated in vacuo. The yellow oil remaining is crystallised by trituration with diisopropylether and the solid product is recrystallised from diisopropylether. White crystals are obtained, melting point 87°-89° C.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05726205uspto-grants-1998_03