Selenium Dioxide → HCID 20434120, compound
Reaction equation
C([O:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])CCC.[Se](=O)=O>>[CH2:6]([O:5][C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:7]([CH:6]=[O:5])=[O:8])[CH2:7][CH2:9][CH3:10]Participants
Procedure
2 g of 2-n-butoxyacetophenone and 1.7 g of selenium dioxide are treated in the same manner as described in Example 6-(1). 2 g of 2-n-butoxyphenylglyoxal thus obtained are dissolved in 6 ml of dimethylsulfoxide, and 1.8 g of 3,4-dimethoxyphenethylamine are added thereto. The solution is stirred at room temperature for 30 minutes. Then, 12 ml of ethanol are added to the solution. After ice-cooling, 0.55 g of sodium borohydride is added gradually to the solution, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is evaporated to remove solvent. Water is added to the thus obtained residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove solvent. The oily residue thus obtained is treated with hydrochloric acid and recrystallized from a mixture of ethanol and ether. 2.6 g of α-(3,4-dimethoxyphenethylaminomethyl)-2-n-butoxybenzylalcohol hydrochloride are obtained. M.p. 128°-129° C.
Sources & evidence
- ORD record
- ord-ee1b9928bb5e4b2e992e1a87d80f42cf
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04131686
Reaction notes
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