alpha-Trifluoroethyl-deoxyanisoin → 4,4'-Dimethoxy-alpha-(n-propyl)-alpha-hydroxy-alpha'-trifluoroethyl-bibenzyl
Reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][CH:4]([C:15]1[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=1)[C:5](=[O:14])[C:6]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[CH:8][CH:7]=1.[CH2:25]([Mg]I)[CH2:26][CH3:27]>>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([C:5]([CH2:25][CH2:26][CH3:27])([OH:14])[CH:4]([CH2:3][C:2]([F:23])([F:24])[F:1])[C:15]2[CH:22]=[CH:21][C:18]([O:19][CH3:20])=[CH:17][CH:16]=2)=[CH:13][CH:12]=1Participants
3
Procedure
To an ethereal solution of n-propyl magnesium iodide (prepared from 0.07 molar n-propyl iodide and magnesium in 100 ml. ether) was added, while stirring, a solution of 16.9 g. (0.05 mole) α-trifluoroethyl-deoxyanisoin (see Example 1a)) and the reaction mixture was heated under reflux for 3 hours, whereafter it was poured into ice - dilute hydrochloric acid and extracted with ether. The ethereal extract was washed with water and an aqueous solution of sodium bisulphite, dried and evaporated to dryness. There was obtained an oily residue of 4,4'-dimethoxy-α-(n-propyl)-α-hydroxy-α'-trifluoroethyl-bibenzyl.
Workup
- temperature