2,6-Dimethylbenzoic acid → (2,6-Dimethylphenyl)methanol

2,6-Dimethylbenzyl alcohol was prepared according to Beaulieu et al. (2000, which is incorporated herein by reference), but was unsuccessful, so a different reducing agent was used. To a suspension of 2,6-dimethylbenzoic acid (1.00 g, 6.65 mmol) in anhydrous THF (10 mL) a solution of BH3(SMe2) in THF was cautiously added under nitrogen atmosphere. The mixture was heated at reflux for 16 hours, then quenched with saturated ammonium chloride (5 mL) and 2 M HCl (10 mL). (CAUTION: vigorous gas evolution!). Organic layer was separated; aqueous layer was extracted three times with ethyl acetate (45 mL each); combined extracts were washed twice with saturated sodium bicarbonate (20 mL each), dried over anhydrous Na2SO4, evaporated, and purified by silica gel chromatography to yield 2,6-dimethylbenzyl alcohol (0.50 g, 51%) as an white solid. 1H NMR (400 MHz, CDCl3): δ 7.08 (m, 3 H, Ph-H), 4.70 (s, 2 H, Ph-CH2), 4.05 (br s, 1 H, OH), 2.40 (s, 6 H, CH3).

1. custom2,6-Dimethylbenzyl alcohol was prepared
2. additionwas cautiously added under nitrogen atmosphere
3. temperatureThe mixture was heated
4. temperatureat reflux for 16 hours
5. customquenched with saturated ammonium chloride (5 mL) and 2 M HCl (10 mL)
6. customOrganic layer was separated
7. extractionaqueous layer was extracted three times with ethyl acetate (45 mL each)
8. washcombined extracts were washed twice with saturated sodium bicarbonate (20 mL each)
9. dry with materialdried over anhydrous Na2SO4
10. customevaporated
11. custompurified by silica gel chromatography

ORD record

ord-19c91bf5648e4c1ea505dcbd36dfe4e0

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497360B2