1-Naphthaldehyde → HCID 11043648, compound

Participants

Reaction Steps

To a solution of 3-bromoanisole (5.61 g, 30.0 mmol) in dry THF (80 mL) was dropwise added n-butyl lithium-hexane solution (1.6 M, 37.5 mL, 60 mmol) under nitrogen at -78° C. The reaction mixture was allowed to warm to r.t. in 2 h and cooled down again to -78° C. prior to addition of 1-naphthaldehyde (4.69 g, 30.0 mmol, in 10 mL THF). The mixture was warmed to r.t. in 3 h, and then quenched with aqueous NH4Cl solution, extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine, dried over MgSO4. Removal of solvents in vacuo provided 3-methoxy-α-(1-naphthyl)benzyl alcohol (4.25 g, 54%). GC-MS (Rt =10.41 min) 264 (M+), 245, 231, 215, 202, 155, 135, 128, 109.

Provenance & Evidence