Acetic Acid → 3-Hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride
Reaction equation
C(O)(=O)C.[ClH:5].Cl.[C:7]([NH:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:17]([OH:32])[CH:16]=1)=[O:14])([CH3:10])([CH3:9])[CH3:8]>CN(C)C=O>[ClH:5].[OH:32][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][C:22](=[O:31])[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[CH:13]([OH:14])[CH2:12][NH:11][C:7]([CH3:10])([CH3:9])[CH3:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Using a procedure similar to that described above in Example 58A, 26 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride was reacted with 16 g. of sodium methoxide in 300 ml. of N,N-dimethylformamide under an atmosphere of nitrogen and then 17 g. of p-anisoyl chloride was added to produce 3-hydroxy-4-(p-anisoyloxy)phenyl tert-butylaminomethyl ketone hydrochloride. This salt was converted to the free base which was treated with acetic acid to yield 35 g. of the acetate salt, m.p. 170°-175° C.(dec.)(uncorr.). By treating this salt in N,N-dimethylformamide with concentrated hydrochloric acid there was obtained 28 g. of the hydrochloride salt, m.p. >235° C.(dec.)(uncorr.). When this hydrochloride is catalytically hydrogenated, using a procedure similar to that described above in Example 30B, there is obtained 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride.
Workup
- customto yield 35 g
- customthere was obtained 28 g
Sources & evidence
- ORD record
- ord-b75b03ceb09e40e680085211c34bd95d
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04138581
Reaction notes
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