Acetyl chloride → (Z)-11-Hexadecenyl acetate

HRID 1389065Notes

Reaction equation

HRID 1389065 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.[O:19]1CCC[CH2:21][CH:20]1OC1CCCCO1.C(Cl)(=O)C>C(O)(=O)C>[C:20]([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:19])[CH3:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86737423HCID 86737423, compound2×

Product 1

HCID 5364711(Z)-11-Hexadecenyl acetateYield 55.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9 g. of (Z)-11-hexadecenol-tetrahydropyranyl ether (Formula III, R=H, Y=tetrahydropyranyl) are dissolved in 25 ml. of acetic acid. 6 ml. of acetyl chloride are added, and the solution is boiled on an oil bath of about 80° C. for 3 hours. The mixture is cooled, poured onto 50 g. of ice, and extracted thrice with a total amount of 200 ml. of hexane. The extracts are combined, washed with 30 ml. of water, dried over magnesium sulfate, filtered, and the solvent is evaporated. The residue is distilled off in fine vacuo. 5.3 g. (55.7%) of (Z)-11-hexadecenyl acetate are obtained; b.p.: 142°-144° C./0.25 mmHG.; 120°-122° C./0.05 mmHg.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto 50 g
  3. extractionof ice, and extracted thrice with a total amount of 200 ml
  4. washwashed with 30 ml
  5. dry with materialof water, dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. distillationThe residue is distilled off in fine vacuo

Sources & evidence

ORD record
ord-132d38875ea64ca6a01b4f6087b4a296
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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