Acetic Acid → HCID 14023756, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of benzaldehyde (212.0 g, 2.0 moles) and methyl chloroacetate (282.0 g, 2.6 mole) in methanol (320.0 g) was cooled to 0° C. under nitrogen. Sodium methoxide (466.0 g of a 30 wt % solution in methanol, 2.5 moles) was added over a period of 2 hours and the mixture was stirred for further 60 minutes at 0° C. The mixture was then allowed to reach 22° C. and stirred for further 2 hours at this temperature. After slow addition of acetic acid (30.0 g, 0.5 moles), toluene (465.0 g) and water (670.0 g) were added consecutively. The aqueous phase was separated and the organic layer was distilled in order to remove water and methanol. After removal of 170.0 g of distillate the mixture was allowed to cool to 25° C. HBr (120.0 g, 1.5 moles) was added over a period of 4 hours keeping the temperature at 25° C. After completion of the addition a mixture of 15.0 g of sodium bicarbonate in 300.0 g water was added dropwise, keeping the temperature between 25 and 30° C. The aqueous layer was then separated, toluene (175.0 g) was added and 115.0 g of toluene was distilled off in order to remove moisture. The mixture was cooled down to 20° C. and toluene (115.0 g) and heptane (260.0 g) were added consecutively. After seeding with 0.5 g of racemic 3-bromo-2-hydroxy-3-phenyl-propionic acid methyl ester, the mixture was slowly cooled to 0° C. and stirred for further 3 hours. The precipitated product was filtered off, washed with 200.0 g heptane and vacuum dried at 45° C. Yield: 234.0 g (0.9 mole, 45%).

Provenance & Evidence