(3-cyclopentyloxy-4-methoxyphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: From 3-hydroxy-4-methoxybenzyl alcohol (50 g, 0.324 mol), cyclopentyloxybromide (70 ml, 0.648 mol), caesium carbonate (72.83 g, 0.222 mol) and sodium iodide (5.63 g, 0.037 mol). Chromatography (SiO2; EtOAc—C6H14. 1:3) to yield the title compound (25.782 g). (Found C, 69.92; H, 8.18. C13H18O3 requires C, 70.25; H, 8.16).

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

Procedure: To a stirred solution of 10.42 g (47.3 mmol) of 3-cyclopentoxy-4-methoxybenzaldehyde in 100 mL of absolute ethanol was added 0.9 g (23.8 mmol) of sodium borohydride in one portion. The mixture was stirred for 1 hour at room temperature after which time the reaction was quenched with excess acetic acid, concentrated and azeotroped to dryness three times with 25 mL portions of toluene. The residue was dissolved in 100 mL of chloroform, washed with two, 25 mL portions of saturated sodium chloride, dried over magnesium sulfate, and concentrated to dryness. Liquid chromatography of the crude oil over 200 g of silica gel with 10% ethyl acetate in hexane provided an analytically pure oil after drying in vacuo. was quenched with excess acetic acid concentrated azeotroped to dryness three times with 25 mL portions of toluene The residue was dissolved in 100 mL of chloroform washed with two, 25 mL portions of saturated sodium chloride dried over magnesium sulfate concentrated to dryness Liquid chromatography of the crude oil over 200 g of silica gel with 10% ethyl acetate in hexane provided an analytically pure oil after drying in vacuo

Conditions: temp:0.00; pressure:0.00; stir: