Hydrochloric Acid → 1-(Chloromethoxy)hexane

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Reaction Steps

102 g of n-hexanol (1 mol) are combined with an aqueous solution of 36 g of formaldehyde gas (1.2 mol). The mixture is slowly agitated, cooled to 1°-5° C and saturated with hydrogen chloride gas. The cold mixture is slowly raised to room temperature. After about 15 hours the mixture is separated and the aqueous portion is discarded. The organic portion is diluted with 50 ml of an inert solvent such as ether, hexane or toluene. The solution is washed twice with 100 ml of ice water. The solvent is removed by distillation under vacuum. The desired chloromethyl-n-hexyl ether is obtained by fractional distillation at a convenient vacuum (between 5-10 mm). The yield is about 55-65% of the theoretical.

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