Methyl iodide → Methyl cyclohexylphenylglycolate, (-)-

Participants

Reaction Steps

To a mixture of (R)-α-cyclohexyl-α-hydroxybenzeneacetic acid (III) (12.2 g, 52.1 mmol) and K2CO3 (10.8 g, 78.2 mmol) in 100 mL of acetone was added methyl iodide (MeI) (13.0 mL, 208 mmol) dropwise at 0° C. (ice bath). After the addition (ca. 1 h) of MeI, the reaction mixture was stirred at room temperature overnight. The mixture was filtered through a pad of Celite and rinsed with acetone twice. The filtrate was concentrated to give a white slurry which was diluted with water and extracted with heptane. The combined extracts were washed with water, brine, dried and concentrated to give the product (R)-IV (11.9 g, 92% yield) as a white solid.

Provenance & Evidence