Water → HCID 54117239, compound

Participants

Reaction Steps

Workup: The reaction mixture obtained as in Example 1a was mixed with 200 ml of water at RT, the upper phase was separated off, and the aqueous phase was extracted three times with 150 ml of hexane each time. The organic phases were combined, washed twice with 150 ml of water and evaporated (rotary evaporator). The residue of 25.5 g was distilled to result in 22.1 g of 1-formyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane with a boiling point of 54-61° C. under 1.5 mbar, which is 90% pure according to gas chromatography (GC), (equivalent to a yield of 85% of theory). A byproduct was ascertained to be 1-hydroxymethyl-2,2,6-trimethyl-7-oxabicyclo[2.2.1]heptane (about 4% of theory). The structure of the product was evident for example from the 1H-NMR spectrum: 250 MHz, (C6D6), δ=1.09 (d, J=8 Hz, 3 H), 4.16 (t, J=6 Hz, 1 H), 9.94 (s, 1 H); [α]D25 =-20.7 (c=1, ethanol).

Provenance & Evidence