Methanol → (R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

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Reaction Steps

(R)-o-chloromandelic acid (5.6 g) was dissolved in 23.1 ml of methanol, and then a catalytic amount of concentrated sulfuric acid (0.12 ml) was added, and heated to reflux for 2 hrs. After cooling, methanol was evaporated under reduced pressure, and the residue was dissolved in dichloromethane, and washed sequentially with 10% aqueous potassium carbonate solution and water. The dichloromethane solution was dried, and evaporated to dryness, to give 5.79 g of (R)-methyl o-chloromandelate as a clear colorless oil. Yield 96%. 1H-NMR (300 MHz, CDCl3) δ 3.52 (d, 1H, J=4.8 Hz), 3.78 (s, 3H), 5.57 (d, 1H, J=4.5 Hz), 7.26-7.31 (m, 2H), 7.37-7.41 (m, 2H); ESI-MS m/z 222.9 [M+Na]+.

Provenance & Evidence