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

To a mixture of 4-butoxymethyl-benzylamine (250 mg) described in Manufacturing Example 43-2, acetic acid (2 mL), and water (2 mL) was added sodium nitrite (1.1 g) at 0° C., which was stirred for 40 minutes at room temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and then extracted. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and then with saturated brine. The solvent was evaporated from the organic layer under a reduced pressure. Methanol (2 mL) and potassium carbonate (360 mg) were added to the residue, and the reaction mixture was stirred for 1.5 hours at room temperature. The solvent was evaporated from the reaction mixture under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the titled compound (200 mg).

1. extractionextracted
2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
3. customThe solvent was evaporated from the organic layer under a reduced pressure
4. additionMethanol (2 mL) and potassium carbonate (360 mg) were added to the residue
5. stirringthe reaction mixture was stirred for 1.5 hours at room temperature
6. customThe solvent was evaporated from the reaction mixture under a reduced pressure
7. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:1)

ORD record

ord-ba8953882be5421ab4d5141e09cdb6db

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183264B2