Acetic Anhydride → HCID 5363514, compound

The 2.4 g of tetradecadienol was dissolved in 55 ml of pentane containing 30 μl of thiophenol in a 100-ml round bottom flask. The flask was heated with a water bath, and the pentane was distilled off. Then a reflux condenser was connected to the flask, and the mixture was heated at 100° C. for 2 hours. The residue was dissolved in 600 ml of heptane which was removed by a rotary evaporator. The thiophenol was removed simultaneously. The yield of isomerized tetradecadienol was 2.01 g (84%). The isomer content by GC analysis was 62% EE, 19% EZ, 15% ZE, 4% ZZ. The tetradecadienol was recrystallized twice at low temperature from pentane to give 0.83 g of a product of 96.2% EE. 10,12-Tetradecadienol in 75 ml pyridine and 5 ml acetic anhydride was refluxed 1.5 hours. After the solution was cooled, 200 ml hexane was added, and the mixture was extracted successively with water, 6N hydrochloric acid (twice), and water. The pentane phase was dried over sodium sulfate, filtered, and the pentane was removed by rotary evaporation, leaving crude product, which was purified by silica gel liquid chromatography (elution in 10% ether/hexane); the yield was 1.0 g (94% based on the alcohol).

1. temperatureAfter the solution was cooled
2. extractionthe mixture was extracted successively with water, 6N hydrochloric acid (twice), and water
3. dry with materialThe pentane phase was dried over sodium sulfate
4. filtrationfiltered
5. customthe pentane was removed by rotary evaporation
6. customleaving crude product, which
7. customwas purified by silica gel liquid chromatography (elution in 10% ether/hexane)

ORD record

ord-a20a9b53cef04cdb8ebfc26c4721af8a

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05236715