Ethanol → 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol

Participants

Reaction Conditions

Reaction Steps

100 g of ethanol, 7.88 g of sodium hydroxide and 30 g of water were added to 75 g of geranylgeranyl p-nitrobenzoate (containing 0.98 g of geranylneryl p-nitrobenzoate and 67.35 g of geranylgeranyl p-nitrobenzoate) obtained as a cake in Example 7. The reaction mixture was stirred at 50°C. for 2 hours and cooled down to room temperature, to which 300 g of toluene and 200 g of water were added. The resulting organic phase was separated and washed twice with 200 g of water, and concentrated under reduced pressure to give 55 g of crude geranylgeraniol. This crude product was subjected to simple distillation (154°C., 0.5 mmHg) to give 42.1 g of a main fraction. The results of the analysis of the obtained fraction with gas chromatography under the same conditions as in Example 14 revealed that it contained geranylgeraniol with a purity of 97.8% and geranylnerol with a purity of 1.2%.

Provenance & Evidence