Acetic Acid → HCID 19095306, compound

Participants

Reaction Conditions

Reaction Steps

7-Chloro-1-(dimethylhydrazono)-1,2,3,4-tetrahydro-2-naphthaleneacetaldehyde dimethyl acetal (16.0 g) was dissolved under argon in 700 ml of tetrahydrofuran and 180 ml of water. The solution was treated in succession with 30.8 g of sodium (meta)periodate, 11.8 g of sodium acetate and 120 ml of acetic acid and stirred at 50° C. for 18 hours. Subsequently, 2000 ml of water were added and the mixture was extracted three times with 500 ml of ethyl acetate each time. The organic phases were washed with 500 ml of a saturated sodium chloride solution, combined, dried over MgSO4 and freed from solvent. The crude product, 18.4 g of dark brown oil, was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:3) as the eluent. There were obtained 4.8 g (35%) of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal.

Provenance & Evidence