Toluene → (2,6-Dimethylphenyl)methanol

To a solution of 2,6-dimethylbenzoic acid (10 g, 66.5 mmol) and potassium carbonate (9.18 g, 66.5 mmol) in dimethylfonnamide (67 ml), was added methyl iodide (8.28 ml, 133.16 mmol) in an ice bath, and the mixture was stirred for 16 hours. To the reaction mixture was added toluene and water, and the organic layer was washed with 3% K2CO3, 1N HCl, and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The oily residue was redissolved in dry THF (135 ml), added to LiAIH4 (3.7 g, 99.8 mmol), and stirred for 4 hours in an ice bath. To the reaction mixture was added 1N HCl slowly followed by ethyl acetate, and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The oily residue was used without further purification.

1. washthe organic layer was washed with 3% K2CO3, 1N HCl, and brine
2. dry with materialThe organic layer was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe oily residue was redissolved in dry THF (135 ml)
6. additionadded to LiAIH4 (3.7 g, 99.8 mmol)
7. stirringstirred for 4 hours in an ice bath
8. additionTo the reaction mixture was added 1N HCl
9. washthe organic layer was washed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customThe oily residue was used without further purification

ORD record

ord-b9f53211304346caba11f615ad91c313

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06924314B2