Acetyl chloride → HCID 12960857, compound

HRID 1389061Notes

Reaction equation

HRID 1389061 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].[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][CH2:16][CH3:17])(=[O:19])[CH3:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86737423HCID 86737423, compound2×

Product 1

HCID 12960857HCID 12960857, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.7 g (0.026 moles) of (Z)-11-heptadecenol-tetrahydropyranyl ether (Formula III, R=CH3, Y=tetrahydropyranyl), 10 ml of acetic acid and 3 ml of acetyl chloride is boiled on an oil bath of about 80° C. for 3 hours. The mixture is cooled, poured onto 30 g. of ice, and extracted with 100 ml. of hexane. The hexane solution is washed with water, dried over magnesium sulfate, the solvent is evaporated, and the residue is distilled in fine vacuo. 2.6 g. (51.6%) of (Z)-11-heptadecenyl acetate (Formula I, R=CH3) are obtained; b.p.: 122°-126° C./0.05 mmHg.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto 30 g
  3. extractionof ice, and extracted with 100 ml
  4. washThe hexane solution is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is evaporated
  7. distillationthe residue is distilled in fine vacuo

Sources & evidence

ORD record
ord-9b48084cec4d46dd9e9d49bb3155aab6
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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