3-Methylnaphthalene-2-carbaldehyde → (3-Methylnaphthalen-2-yl)methanol

Temperature

0 °C

To a stirred solution of 3-methylnaphthalene-2-carboxaldehyde (3.40 g, 20 mmol) in dry THF (200 mL) cooled to 0° C. was added lithium aluminum hydride (LAH, 380 mg, 10 mmol), in portions over 10 minutes. The resulting solution was stirred at 0° C. for 1.5 hours. Excess LAH was quenched by the addition of H2O (50 mL) and the THF was removed in vacuo. The residue was diluted with 1N HCl (150 mL) and extracted with Et2O (3×200 mL). The organics were dried (MgSO4) and concentrated in vacuo to give the crude product as a tan solid. This material was purified by preparative HPLC (SiO2 : 1:1 CH2Cl2 /hexane) to afford the title compound as a white solid (2.47 g, 72%).

1. customExcess LAH was quenched by the addition of H2O (50 mL)
2. customthe THF was removed in vacuo
3. additionThe residue was diluted with 1N HCl (150 mL)
4. extractionextracted with Et2O (3×200 mL)
5. dry with materialThe organics were dried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto give the crude product as a tan solid
8. customThis material was purified by preparative HPLC (SiO2 : 1:1 CH2Cl2 /hexane)

ORD record

ord-915b9ba038104c8bb52b5dd8c4c8e71b

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04895861