2-Chlorotoluene → 3-(o-Toluyloxy)-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone
Reaction equation
[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[C:11]([OH:23])[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C1([O-])C=CC=CC=1.[Na+].[C:35]1([CH3:42])[C:36](Cl)=[CH:37][CH:38]=[CH:39][CH:40]=1>>[C:1]([NH:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[C:11]([O:23][C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:42])[CH:10]=1)=[O:8])([CH3:4])([CH3:3])[CH3:2]Participants
5
Procedure
Following a procedure similar to that described in Example 30A above, when 3-hydroxy-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone is interacted with one equivalent of sodium methoxide and the resulting sodium phenolate salt is reacted with o-toluyl chloride there is obtained 3-(o-toluyloxy)-4-(p-toluyloxy)phenyl tert-butylaminomethyl ketone which reacts with hydrochloric acid to yield the hydrochloride salt. When this hydrochloride is catalytically hydrogenated, using the procedure described above in Example 30B, there is obtained 3-(o-toluyloxy)-4-(p-toluyloxy)-alpha-(tert-butylaminomethyl) benzyl alcohol hydrochloride.
Sources & evidence
- ORD record
- ord-2c9881cc7eae40eeab14eb72482740fa
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04138581
Reaction notes
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