반응 #582501

ord-a876761294254d60891a607502043b2f

반응 방정식

O=Cc1ccc(O)cc1
4-Hydroxybenzaldehyde
C1=COCCC1
dihydropyran
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulphonate
O=Cc1ccc(OC2CCCCO2)cc1
oil
수율 87.0%
O=Cc1ccc(OC2CCCCO2)cc1
4-(Tetrahydro-pyran-2-yloxy)-benzaldehyde
수율 87.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척The mixture was washed with dilute aqueous sodium hydroxide solution (2×300 ml), water (200 ml), brine (300 ml)
  2. 2
    건조finally with water (250 ml), dried over sodium sulphate
  3. 3
    기타evaporated to dryness

실험 절차

4-Hydroxybenzaldehyde (43.4 g, 0.355 mol), dihydropyran (44.4 ml, 0.495 mol), pyridinium p-toluenesulphonate (11.6 g, 0.046 mol, 0.1 mol equiv.) and dichloromethane (300 ml) were stirred for 16 h at room temperature. The mixture was washed with dilute aqueous sodium hydroxide solution (2×300 ml), water (200 ml), brine (300 ml), and finally with water (250 ml), dried over sodium sulphate and evaporated to dryness to leave a dark brown oil(63 g, 87%). This was used without further purification in the following step 1CW02. 1H NMR showed expected signals.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06939479B2uspto-grants-2005_09