METHYL 2-METHYL-4-BENZYLOXY-PHENYLACETATE synthesis

Yield:-

Reaction Conditions:

with potassium carbonate in DMF (N,N-dimethyl-formamide) at 20;

Steps:

38

Reference Example 38; Methyl [4-(benzyloxy)-2-methylphenyl]acetate [] To a solution of [4-(benzyloxy)-2-methylphenyl]acetonitrile (2.97 g) in tetrahydrofuran (30 ml) - ethanol (30 ml) was added 8 N sodium hydroxide (30 ml) and the mixture was heated under reflux overnight. The mixture was acidified with 6 N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (50 ml), and potassium carbonate (3.46 g) and iodomethane (1.8 ml) were added thereto. The mixture was stirred at room temperature overnight and then diluted with ethyl acetate and washed with water and saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane - ethyl acetate = 5 : 1) to obtain an objective product (1.13 g) as an oily matter.1H-NMR (CDCl3) δ 2.27 (3H, s), 3.57 (2H, s), 3.67 (3H, s), 5.03 (2H, s), 6.74-6.83 (2H, m), 7.10 (1H, d), 7.30-7.45 (5H, m).

References:

EP1535915,2005,A1 Location in patent:Page/Page column 85-86