Acetic Anhydride → HCID 12960857, compound

HRID 1389063Notes

Reaction equation

HRID 1389063 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][CH3:17].[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][CH2:16][CH3:17])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5283301HCID 5283301, compound2×

Product 1

HCID 12960857HCID 12960857, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The obtained (Z)-11-heptadecenol (Formula II, R=CH3) is added to a mixture of 5 ml. of dry pyridine and 3.5 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. 2.25 g (42%) of (Z)-11-heptadecenyl acetate (Formula I, R=CH3) are obtained; this compound is identical with the product obtained in 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-06f2083aa21240548febb9354bc4cf7a
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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