Aluminium lithium hydride → HCID 118307145, compound

Participants

Reaction Steps

To a mixture of methyl 2-allyl-4-methylbenzoate (220 mg, 1.156 mmol) in THF (2 mL) was added LAH (2.313 mL, 2.313 mmol) and the reaction mixture was stirred at rt for 1 h. It was then added NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (2-allyl-4-methylphenyl)methanol (150 mg, 0.925 mmol, 80% yield) as an oil. 1H NMR (500 MHz, CDCl3) δ 7.31-7.25 (m, 1H), 7.10-7.03 (m, 2H), 6.03 (ddt, J=16.9, 10.4, 6.3 Hz, 1H), 5.13-5.00 (m, 2H), 4.69 (d, J=5.2 Hz, 2H), 3.48 (d, J=6.3 Hz, 2H), 2.36 (s, 3H), 1.53 (t, J=5.7 Hz, 1H).

Provenance & Evidence