Ethyl Acetate → HCID 54535871, compound

Participants

Reaction Steps

6-Chloro-1-(dimethylhydrazono)-1,2,3,4-tetrahydro-2-naphthaleneacetaldehyde dimethyl acetal (10.3 g) was dissolved under argon in a mixture of 500 ml of tetrahydrofuran and 265 ml of 0.067M phosphate buffer of pH value 7. The solution was treated with 8.7 g of copper(II) chloride dihydrate and stirred at room temperature for 18 hours. 400 ml of ethyl acetate were added to the reaction mixture and it was washed twice with 500 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time. The aqueous wash phases were extracted three times with 200 ml of ethyl acetate each time, the organic phases were combined, dried over MgSO4 and freed from solvent. The crude product, 8.2 g of brown oil, was chromatographed on 330 g of silica gel with ethyl acetate/hexane mixtures (1:6 to 1:4) as the eluent. There were obtained 2.1 g (24%) of 6-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal besides 3.2 g (43%) of 6-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde.

Provenance & Evidence