Prop-1-yn-1-ol → 2,4-Hexadiyn-1,6-diol monophenylurethane
Reaction equation
[C:1]([OH:4])#[C:2][CH3:3].[CH2:5]([OH:8])[C:6]#[CH:7].[C:9]1([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:5]([OH:8])[C:6]#[C:7][C:3]#[C:2][CH2:1][OH:4].[C:9]1([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
3
Procedure
The monomer 2,4-hexadiyn-1,6-diol-monophenylurethane is synthesized by the unsymmetrical coupling reaction of propyne-1-ol and 2-propyne-1-ol-phenylurethane and is purified by recrystallization of the crude product from ethyl acetate/petroleum ether. Recrystallization of a 0.4 gm sample from 100 ml of a 10:90 acetone/petroleum ether solvent mixture by slow evaporation at room temperature gives approximately 5 cm long needle-like crystals which turn pink upon exposure to light.
Workup
- customis purified by recrystallization of the crude product from ethyl acetate/petroleum ether
- customRecrystallization of a 0.4 gm sample from 100 ml of a 10:90 acetone/petroleum ether solvent mixture