Acetyl chloride → HCID 12960857, compound

HRID 1389064Notes

Reaction equation

HRID 1389064 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 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4 g (0.012 moles) of 1-(1-ethoxyethoxy)-11(Z)-heptadecene (Formula III, R=CH3, Y=CHCH3OCH2CH3) are added to a mixture of 8 ml. of acetic acid and 2.5 ml. of acetyl chloride, and the mixture is boiled on an oil bath of about 80° C. for 3 hours. The mixture is cooled, poured onto 20 g. of ice and extracted with 100 ml. of hexane. The extract is washed with water, dried over magnesium sulfate, filtered, and the solvent is evaporated. The residue is distilled in fine vacuo. 2.2 g. (62%) of (Z)-11-heptadecenyl acetate are obtained; b.p.: 120°-126° C./0.05 mmHg. This product is identical with the compound obtained in step (A) above.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto 20 g
  3. extractionof ice and extracted with 100 ml
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. distillationThe residue is distilled in fine vacuo

Sources & evidence

ORD record
ord-9053ed61857e42629c70c4784880ed22
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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