Nitrogen → 3-(3',4'-Dimethoxyphenyl)-1-propanol

Participants

Reaction Steps

To a 5 1, 3-neck flask, fitted with a condenser, mechanical stirrer and septum inlet, was added by needle/N2 pressure a solution of lithium aluminum hydride in THF (1M, 912 cc). Methyl 3-(3,4-dimethoxyphenyl)propionate (213 g, 0.95 mole) was dissolved in dry THF (total volume 900 cc and the resulting solution was added dropwise over a period of 5 hours using needle/N2 pressure to the stirred LAH solution at a rate to maintain gentle reflux under a continuous N2 atmosphere. The reaction mixture was stirred overnight at room temperature, cooled in an ice/acetone bath and treated dropwise over about 2 hours with saturated NH4Cl solution (104 cc), the nitrogen pressure being continued to this point. After stirring for several hours, the mixture was filtered and the salts were washed with dry THF. The filtrate was evaporated in vacuo to a light yellow oil; yield: 160 g. The salts from the above filtration were air-dried for several days, combined with CH2Cl2 (700 cc), stirred overnight and filtered. The filtrate was evaporated in vacuo to give an additional 26 g of product. The overall yield of a light yellow oil was: 186 g (100%).

Provenance & Evidence