Acetic Anhydride → HCID 53940283, compound

HRID 974738Notes

Reaction equation

HRID 974738 reaction equation
C(#N)C=CCCCCCCC.[CH2:12]([OH:27])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26].CCCCCC.[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1>[C:34]([O:27][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8058HexaneHCID 1064592-DecenenitrileHCID 54322293HCID 54322293, compound

Product 1

HCID 53940283HCID 53940283, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The pentadecadiene (D) (5.9 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water were added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3.1 g of crude 8,10-pentadecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.5 g (66% yield based on the decenenitrile (B)). 8,10-Pentadecadienol 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 2.8 g (94% based on the alcohol). The product was 39% EE and 61% EZ by GC analysis.

Workup

  1. customwas purified by silica gel liquid chromatography
  2. washUnwanted side products were eluted with 10% ether/hexane
  3. washthe alcohol was eluted with 50% ether/hexane
  4. customgiving 2.5 g (66% yield
  5. temperatureAfter the solution was cooled
  6. extractionthe mixture was extracted successively with water, 6N hydrochloric acid (twice), and water
  7. dry with materialThe pentane phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe pentane was removed by rotary evaporation
  10. customleaving crude product, which
  11. customwas purified by silica gel liquid chromatography (elution in 10% ether/hexane)

Sources & evidence

ORD record
ord-1cc1d02ce4f34a81950025f262f9b1b9
Source dataset
uspto-grants-1997_03
Patent number
US05607670

Reaction notes

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