3-(BENZYLOXY)-O-TOLUIDINE synthesis

Yield:65361-82-2 100%

Reaction Conditions:

Stage #1: 2-benzyloxy-6-nitrotoluenewith acetic acid;zinc in methanol at 0; for 1 h;
Stage #2: with sodium hydrogencarbonate in water;ethyl acetate;

Steps:

23

(Referential Example 23) Synthesis of 3-benzyloxy-2-methylaniline (referential compound 23) Zinc (52.3 g, 800 mmol) was added, in a divided manner, at 0°C to a solution of 49.3 g (203 mmol) of 2-benzyloxy-6-nitrotoluene (referential compound 22-1) in 400 ml of methanol and 200 ml of acetic acid in an argon stream with stirring and the mixture was stirred for 1 hour. After the reaction was finished, the reaction solution was poured into 1,600 ml of water and the mixture was extracted with 1,500 ml of ethyl acetate. The organic layer was successively washed with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 44.0 g of the title compound as a brown oily substance (yield: quantitative). Rf value: 0.22 (n-hexane: ethyl acetate = 4:1 (v/v)) Mass spectrum (EI, m/z): 213 (M⁺) ¹H-NMR spectrum (CDCl₃, δ ppm): 2.11 (s, 3H), 3.64 (brs, 2H), 5.05 (s, 2H), 6.36-6.39 (m, 1H), 6.41 (d, J = 8.3Hz, 1H), 6.93-6.99 (m, 1H), 7.29-7.46 (m, 5H)

References:

EP1679308,2006,A1 Location in patent:Page/Page column 43