Hydrochloric Acid → Hydrochloric Acid
Reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[C:13](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[CH2:14][CH3:15])=[CH:8][CH:7]=1.[ClH:30]>>[CH3:29][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9](/[C:12](/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[C:13](/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)\[CH2:14][CH3:15])=[CH:10][CH:11]=1.[ClH:30]Participants
Procedure
A method for the production of E-1-[4'-(2-dimethylaminoethoxy)-phenyl]-1-(3 '-hydroxyphenyl)-2-phenyl-1-butene of formula (I) ##STR9## which comprises the steps of a) heating the compound of formula (II) ##STR10## where R is an easily hydrolyzable protecting group at a temperature within the range of 70°-80° C. for a time within the range of 4-6 hours in the presence of an organic solvent and HCl gas and then cooling the reaction to a temperature within a range of -5° to 5° C. for a time within the range of 10-14 hours to obtain E/Z-1-[4'-(2-dimethylaminoethoxy)-phenyl]-1-(3'-hydroxyphenyl) -2-phenyl-1-butene×hydrochloride of formula (IIIa), and ##STR11## b) heating the compound of formula(IIIa) at a temperature within the range of 50°-60° C. for a time within the range of 10-24hours in the absence of an organic solvent and in the presence of 40-50% by volume suifuric acid or 32-37% hydrochloric acid, and alkalinizing the reaction mixture to obtain the compound according to formula (I).
Workup
- customwithin the range of 70°-80° C.
- customwithin the range of 4-6 hours
- temperaturecooling
- customthe reaction to a temperature within a range of -5° to 5° C. for a time within the range of 10-14 hours
Sources & evidence
- ORD record
- ord-a05ceae3fe1143d380b6eb6d10602442
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05693863
Reaction notes
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