HCID 11558022, compound → (2E,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol

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Reaction Steps

A solution of 1 g (0.0038 mol) of ethyl (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate in 8 ml of toluene is treated dropwise at -5° to -10° with 9.45 ml of a solution of diisobutylaluminium hydride in toluene (1.2 mol/l, i.e. 3.0 mol equivalents). The solution is stirred at the same temperature for 1 hour under argon. The reaction mixture is poured into an ice-water mixture and extracted with ether. After drying and removing the solvent the residue is chromatographed on silica gel with ether-hexane 1:1. There is obtained (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol which has the following bands in the IR spectrum: 3323 cm-1, 1668 cm-1, 1446 cm-1, 1377 cm-1, 1001 cm-1.

Provenance & Evidence