Acetophenone → 1-(3-Vinylphenyl)-1-phenylethyl alcohol
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:10]([C:12]1[CH:13]=[C:14]([Mg]Br)[CH:15]=[CH:16][CH:17]=1)=[CH2:11]>>[CH:10]([C:12]1[CH:13]=[C:14]([C:1]([OH:3])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:2])[CH:15]=[CH:16][CH:17]=1)=[CH2:11]Participants
3
Procedure
A method to use acetophenone (formula VIII) as a starting material is described. Acetophenone is reacted with a Grignard reagent of 3-vinylphenylmagnesium bromide (formula VII) to obtain 1-(3-vinylphenyl)-1-phenylethyl alcohol (formula V) (hereinafter referred to as "VPA"). The reaction product is then dehydrated in the presence of potassium hydrogensulfate to form 1-(3-vinylphenyl)-1-phenylethylene (formula I). This Grignard addition reaction is carried out at a temperature in the range of 0° to 100° C., preferably 20° to 80° C. The dehydration is carried out at 170° to 250° C., preferably 190° to 230° C., under a reduced pressure. The quantity of Grignard reagent is 1.0 to 1.2 equivalents relative to the acetophenone. ##STR7##
Sources & evidence
- ORD record
- ord-89c97cbc4e104cba83db2b8c69076ce2
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04822934
Reaction notes
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