2-Naphthalenemethanol, 1-nitro- synthesis

Yield:265126-05-4 99%

Reaction Conditions:

with sodium tetrahydridoborate in ethanol at 0 - 20; for 2 h;

Steps:

Using the general procedure for the reduction of substituted 2-nitrobenzaldehyde the desired product was obtained as a dark yellow solid, 1 g, >99 % yield. R.f. 0.59 (EtOAc), m.p 78-80 °C,¹H NMR (CDCl₃, 270 MHz,): δ 2.32 (IH, br.s, OH), 4.82 (2H, s, CH₂), 7.48-7.65 (3H, m, ArH), 7.81-7.90 (2H, m, ArH), 7.99 (IH, d, J= 8.4, ArH). General Procedure for the Reduction of Substituted 2-Nitrobenzaldehyde.solution of the desired substituted 2-nitrobenzaldehyde in EtOH (5 ml/mrnol) was cooled to 0⁰C and to this was added NaBH₄ (1.5 eq) and the resulting solution was stirred at r.t. for 2 h. The EtOH was removed in vacuo and sat. NH₄Cl solution was added and the mixture was then extracted with DCM and dried (MgSO₄). It was then evaporated in vacuo to yield the desired substituted 2-nitrobenzyalcohol.

References:

WO2009/66072,2009,A2 Location in patent:Page/Page column 55-56; 66