Ethyl Acetate → HCID 19095266, compound

Participants

Reaction Steps

5-Chloro-1-(dimethylhydrazono)-1,2,3,4-tetrahydro-2-naphthaleneacetaldehyde dimethyl acetal (47.5 g) was dissolved under argon in a mixture of 2300 ml of tetrahydrofuran and 780 ml of 0.067M phosphate buffer of pH value 7. The solution was treated with 26.1 g of copper(II) chloride dihydrate and stirred at room temperature for 16 hours. 2000 ml of ethyl acetate were added to the reaction mixture and it was washed three times with 2000 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time. The aqueous wash phases were extracted once with 1500 ml of ethyl acetate and once with 1000 ml of ethyl acetate, the organic phases were combined, dried over MgSO4 and freed from solvent. There were obtained 42.2 g of crude 5-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal which was processed without purification.

Provenance & Evidence