Toluene → Methyl 6-(Hydroxymethyl)-2-naphthoate

Temperature

-50 °C

Red-Al (0.61 ml of a 65% toluene solution, a product of Aldrich, 2.1 mmol) was added dropwise to a solution of commercially available dimethyl 2,6-naphthalenedicarboxylate (500 mg, 2.1 mmol) in anhydrous tetrahydrofuran (120 ml) cooled to −50° C. The resulting mixture was stirred at −50° C. for 1 hour and then at room temperature for 1.5 hours. To the reaction mixture were added sequentially ethyl acetate, water, 0.5N aqueous sodium potassium (+)-tartrate solution and the mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was chromatographed on a silica gel column using ethyl acetate-hexane (2:1) as the eluant to obtain methyl 6-hydroxymethyl-2-naphthalenecarboxylate (288 mg, yield 65%) as a white solid which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

1. waitat room temperature for 1.5 hours
2. customthe mixture was partitioned between ethyl acetate and water
3. washThe organic layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was chromatographed on a silica gel column

ORD record

ord-9a493d921c5b45ceb60bbb7fd618a786

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06653330B2