(1R)-2-chloro-1-(2,4-dichlorophenyl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (R)-2-Chloro-(2′,4′-dichlorophenyl)-1-ethanol (1.95 g, 8.65 mmol) was dissolved in 60 mL of anhydrous acetone (4A molecular sieves). Then NaI (7 g, 46.70 mmol) was added to the solution and the solution refluxed for 3 hours under nitrogen. Upon cooling to room temperature, the solution was poured into 160 mL of hexanes/ethyl acetate (3:1), and filtered to remove excess NaI which had precipitated. The filtrate was evaporated to dryness in vacuo, and the residue treated with ether and decanted from the solid NaI. Upon removal of ether, the product was obtained as white solid. Yield: 2.40 g (88%). the solution refluxed for 3 hours under nitrogen filtered to remove excess NaI which had precipitated The filtrate was evaporated to dryness in vacuo the residue treated with ether decanted from the solid NaI Upon removal of ether the product was obtained as white solid

Conditions: temp:-25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution containing 16 g (49.90 mmol) of (−)-DIP-Cl in 30 mL of anhydrous THF, at −25° C. (dry ice, CCl4), under nitrogen, was added 10 g (44.74 mmol) of 2,2′,4′-trichloroacetophenone. The stoppered solution was stirred at −25° C. for about 7 hours, and then at room temperature overnight. THF was removed in vacuo, and (+)-α-pinene was removed under high vacuum at room temperature overnight. The resulting viscous colorless oil was dissolved in 200 mL of anhydrous ether, and cooled to 0° C. Diethanolamine (10.50 g, 0.10 mol) was added to the filtrate, and stirring was continued for 3 hours at room temperature. The white solid obtained was removed by filtration and washed with anhydrous ether. The colorless solution was evaporated to dryness to yield a viscous colorless oil. This oil was flash chromatographed on silica gel, first with hexanes to remove (+)-α-pinene. The product was eluted from the column with 93% hexanes/7% acetone to yield 11.30 g of a white solid. This solid was crystallized from hexanes at 0° C. Yield: 5.75 g (57%); TLC: 95% hexanes/5% acetone, Rf=0.10. at room temperature overnight THF was removed in vacuo, and (+)-α-pinene was removed under high vacuum at room temperature overnight The resulting viscous colorless oil was dissolved in 200 mL of anhydrous ether cooled to 0° C stirring was continued for 3 hours at room temperature The white solid obtained was removed by filtration washed with anhydrous ether The colorless solution was evaporated to dryness to yield a viscous colorless oil chromatographed on silica gel, first with hexanes to remove (+)-α-pinene The product was eluted from the column with 93% hexanes/7% acetone