Acetic Anhydride → (Z)-11-Hexadecenyl acetate

HRID 1389067Notes

Reaction equation

HRID 1389067 reaction equation
[CH2:1]([OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16]C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:18][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH3:16])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5283301HCID 5283301, compound2×

Product 1

HCID 5364711(Z)-11-Hexadecenyl acetateYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The obtained (Z)-11-hexadecenol (Formula II, R=H) is added to a mixture of 5 ml. of dry pyridine and 4 ml. of acetic anhydride, and the mixture is stirred at 0° C. for 3 hours. The solution is poured onto ice and extracted with methylene chloride. The extract is washed with water, 3% aqueous sulfuric acid and again with water, dried over magnesium sulfate, filtered, and the solvent is evaporated. The residue is distilled in fine vacuo. 2.2 g (40%) of (Z)-11-hexadecenyl acetate (Formula I, R=H) are obtained; the product is identical with the substance obtained according to step (A) above.

Workup

  1. additionThe solution is poured onto ice
  2. extractionextracted with methylene chloride
  3. washThe extract is washed with water, 3% aqueous sulfuric acid and again with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. distillationThe residue is distilled in fine vacuo

Sources & evidence

ORD record
ord-7f242019fb574f9b83fc8cbd5725b13d
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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