Trityl chloride → 1,2:4,5-Bis-O-(1-methylethylidene)xylitol

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Reaction Steps

Under nitrogen, 47.0 g of the diisopropylideneribitol isomers (202 mmol, containing ˜59.5 mmol of primary alcohol) was dissolved, along with triethyl amine (16.9 mL, 121 mol, 0.6 eq) and DMAP (396 mg, 3.238 mmol, 0.016 eq), in 225 mL dry dichloromethane. Trityl chloride (22.6 g, 80.9 mmol, 0.4 eq) was taken up in a minimal amount of dry dichloromethane and added dropwise to the stirred reaction solution. The mixture was stirred over night at room temperature. The reaction mixture was poured into a saturated solution of sodium bicarbonate and stirred for 30 min. The mixture was extracted three times with diethyl ether. The pooled organic phases were washed once with brine, dried over magnesium sulfate, concentrated on the rotary evaporator and residual volatiles removed under high vacuum. The residue was distilled at 135-140° C., 1.2-1.6 torr, using Kugelrohr distillation to yield 29.3 g of bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol as a colorless oil.

Provenance & Evidence