Acetic Acid → (4-Butoxymethyl-phenyl)-methanol

To a mixture of 4-butoxymethyl-benzylamine (250 mg, 1.3 mmol) described in Manufacturing Example 33-1-2, acetic acid (2 mL) and water (2 mL) was added sodium nitrite (1.1 g, 16 mmol) at 0° C., which was stirred for 40 minutes at room temperature. The reaction mixture was partitioned into ethyl acetate and water. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Methanol (2 mL) and potassium carbonate (360 mg, 2.6 mmol) were added to the residue, and the reaction mixture was stirred for 1.5 hours at room temperature. The reaction mixture was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the title compound (200 mg, 78%).

1. customThe reaction mixture was partitioned into ethyl acetate and water
2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride
3. customthe solvent was evaporated under a reduced pressure
4. stirringthe reaction mixture was stirred for 1.5 hours at room temperature
5. concentrationThe reaction mixture was concentrated under a reduced pressure
6. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:1)

ORD record

ord-79b2d9dd51b344faa4f85164b180b4ad

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507530B2