(2E,4E)-dodeca-2,4-dien-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2E,4E)-Dodeca-2,4-dien-1-ol (4.95 g) was dissolved in dry toluene (110 ml) and diphenylphosphinyl azide (7.92 g) was added. DBU (4.91 ml) was added dropwise. The mixture turned opaque under evolution of heat. The solvent was evaporated and diethyl ether was added to the residue. The reaction mixture was washed with 1M HCl, 1M NaOH and brine and the organic layer was dried over sodium sulfate, filtered and concentrated to give a light yellow liquid. The crude product was filtered over silica gel. of heat The solvent was evaporated diethyl ether was added to the residue The reaction mixture was washed with 1M HCl, 1M NaOH and brine the organic layer was dried over sodium sulfate filtered concentrated to give a light yellow liquid The crude product was filtered over silica gel

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under nitrogen atmosphere, (2E,4E)-ethyl dodeca-2,4-dienoate (6.1 g) was dissolved in n-heptane (120 ml) and cooled to −70° C. DIBAL-H in hexanes (82 ml) was added dropwise and the mixture was stirred at −70° C. for 45 min. Brine (60 ml) and diethyl ether (100 ml) were added and the mixture was stirred for 45 min while warming to RT. The organic layer was separated and washed with 1N HCl, dried over sodium sulfate, filtered and concentrated. A colorless liquid was isolated that solidified upon slight cooling. the mixture was stirred for 45 min while warming to RT The organic layer was separated washed with 1N HCl dried over sodium sulfate filtered concentrated A colorless liquid was isolated that solidified upon slight cooling