Hydrochloric Acid → HCID 54070919, compound

Participants

Reaction Steps

9.6 g (35 mmol) of trans-1-formyl-8-methoxy-3a,4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (5) are dissolved in 75 mL of n-propanol and mixed with 25 mL of conc. hydrochloric acid and 15 mL of water. The mixture is refluxed for 12 h, the alcohol is eliminated in vacuo and diluted with 800 mL of water. The mixture is extracted once with 150 mL of ethyl acetate (discarded), the aqueous phase is made alkaline with sodium hydroxide and extracted three times with 200 mL ethyl acetate. The combined organic phases are dried over MgSO4 and the solvent is eliminated in vacuo. 8.6 g (100%) of trans-8-methoxy-3a,4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (6) are obtained as an oil.

Provenance & Evidence