Aluminium lithium hydride → (2,4-Diethylphenyl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[CH:15][C:10]=1[CH2:11][OH:12])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of lithium aluminum hydride (0.47 g, 11.8 mmol) in anhydrous THF (20 mL) at room temperature under nitrogen was added a solution of methyl 2,4-diethylbenzoate (1.5 g, 7.8 mmol) in THF (15 mL) with stirring over a period of ˜5 min. The resulting mixture was stirred at room temperature for 60 min and was then quenched by slow addition of ethyl acetate (until bubbling stopped). The mixture was partitioned between ethyl acetate and 1N HCl (aq). The aqueous layer was separated and extracted with ethyl acetate. Organic layers were combined, dried (MgSO4), and evaporated to dryness to give 1.3 g of the desired alcohol as a clear oil (yield of 100%). 1H NMR (300 MHz, CDCl3) δ 1.13 (t, 3H), 1.17 (t, 3H), 2.58 (q, 2H), 2.61 (q, 2H), 4.43 (d, 2H), 5.02 (t, 1H), 7.05-7.11 (m, 3H).