Dichloromethane → HCID 19777598, compound

Participants

Reaction Steps

A mixture of 178 mg (0.905 mmole) of 1-chloro-1,2,2-triethoxyethane (produced in accordance with Example IV) and 206 mg (1.43 mmoles) of sodium benzoate in 3.00 mL of N,N-dimethylformamide, spectrophotometric-grade, commercially available from Aldrich Chemical Co., Milwaukee, Wis., was stirred, while being protected from exposure to atmospheric moisture, at room temperature for 21 hours. The mixture was diluted with 20 mL of 3:1 (volume/volume) ether:methylene chloride; and the organic layer was washed five times with 25 mL portions of I0% aqueous sodium chloride to ensure removal of dimethylformamide. The washed organic layer was subsequently dried over anhydrous sodium sulfate and filtered. Removal of the volatile organic material under reduced pressure afforded 212 mg (83% yield) of the title compound, the identity and purity of which were ascertained by proton NMR analysis [two doublets (J=5.5 Hz), one at δ4.63 (CH3CH2OCHOCH2CH3), the other at δ6.07 (CHOC(=O)C6H5)]. The title compound was subsequently saponified by use of potassium carbonate (2 equivalents) in 4:1 (volume/volume) methanol:water at 0° C. for 5 hours to afford glyoxal mono(diethyl acetal) and the corresponding hydrate (CH3CH2O)2CHCH(OH)2 and hemiacetal ##STR10## in high yield. Heating the latter mixture in toluene as described in Example XVIII affords glyoxal mono(diethyl acetal) as methanol and water are distilled out of the mixture.

Provenance & Evidence