3,4-Dichlorophenol → 1,2-Dichloro-4-(2,2-diethoxyethoxy)benzene

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Reaction Conditions

Reaction Steps

Potassium hydroxide (66 g) and 3,4-dichlorophenol (163 g) were placed in a reaction flask equipped with a distillation head, dropping funnel, thermometer and mechanical stirrer. This mixture was gradually heated to achieve solution and then 250 g of chloroacetaldehyde diethyl acetal was added while the temperature was maintained at 90° C. After the addition was complete, the temperature was allowed to increase in order to distill off water and unreacted chloroacetaldehyde diethyl acetal. The distillate separated into layers which were recovered by conventional techniques. The lower layer was dried and subsequently returned to the reaction flask where it was heated (without distillation) at 190° C. for 2 hours. The contents of the reaction flask were cooled to room temperature and poured into an ice-water mixture and extracted with methylene chloride. The methylene chloride solution was washed with 300 ml of 2N NaOH, dried, and distilled. After removal of the starting material, 276.3 g of the desired, 3,4-dichlorophenoxyacetaldehyde diethyl acetal was obtained, b.p. 125° C. (0.04 mm Hg).

Provenance & Evidence