Methyl 3-ethylbenzoate → (3-Ethylphenyl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](OC)=[O:13])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[CH:17][CH:18]=1)[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium aluminum hydride (3.1 mL of 1.0 M solution in THF, 3.1 mmol) was added to a solution of methyl 3-ethylbenzoate (500 mg, 3.05 mmol) in THF (12 mL) at 0° C. After 2 h at 0° C., the reaction was quenched by the addition of saturated aqueous Rochelle's salt (50 mL) and stirred vigorously overnight at room temperature. The reaction mixture was extracted with Et2O (3×100 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford (3-ethylphenyl)methanol which was shown to be ˜90% pure by 1H NMR analysis and was taken on without further purification.