Allyl Alcohol → 1-Allyloxyethoxyethane

반응식

[CH2:1]([OH:4])[CH:2]=[CH2:3].[CH:5]([O:7][CH2:8][CH3:9])=[CH2:6].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>>[CH2:5]([O:7][CH:8]([O:4][CH2:1][CH:2]=[CH2:3])[CH3:9])[CH3:6]

참가 물질

반응물 3

HCID 7858Allyl Alcohol

HCID 8023Ethyl vinyl ether

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

생성물 1

HCID 127395961-Allyloxyethoxyethane

실험 절차

Allyl alcohol (46.8 ml. 40 g., 0.69 mol) and ethyl vinyl ether (98.8 ml., 74.5 g., 1.033 mols) were stirred together at -12°. dl-Camphorsulfonic acid (150 mg.) was added acid and stirring continued for 3 hours at that temperature. The mixture was then washed 1×100 ml. saturated NaHCO3, 1×100 ml. brine, dried and stripped to yield title product as an oil (100 ml., essentially quantitative yield). 1H-nmr: 1.14 (t, 3H), 1.29 (d, 3H), 3.56 (dp, 2H), 4.06 (m, 2H), 4.75 (q, 1H), 5.26 (m, 2H), 5.99 (m, 1H).