Ethylene Glycol → HCID 68865936, compound

Participants

Reaction Steps

A soln. of 2.0 g of 5-isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (9.8 mmol) in 100 ml cyclohexane was treated with 1.8 g ethyleneglycol (2.9 mmol, 3.0 eq.) and 0.2 g para-toluenesulfonic acid mono hydrate (1.0 mmol 0.1 eq.). The soln. obtained was heated at reflux for 3 h (Dean-Stark apparatus), cooled and poured into aq. sat. NaHCO3 soln. (100 ml). Extraction with MTBE (2×80 ml) followed by washing of the aq. phases with H2O (100 ml) and aq. sat. NaCl soln. (150 ml), drying of org. phases over MgSO4 led to 2.6 g of crude product. FC (SiO2, hexane/MTBE 19:1) gave 0.76 g (31%) of compound 6 as colorless liquid. The boiling point of the end product is 130° C. at 0.09 mbar. Rf (hexane/MTBE 19:1) 0.47.

Provenance & Evidence