Acetic Anhydride → (E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienyl acetate

HRID 1589534Notes

Reaction equation

HRID 1589534 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][OH:5].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5365870geranylcitronellol

Product 1

HCID 20246093(E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml. of pyridine was dissolved 2.9 g. of the product obtained in Example 17, and to the solution was added 1.1 g. of acetic anhydride under stirring. The resulting mixture was then refluxed for 1 hour. The reaction mixture was then poured into 50 ml. of water, and was then extracted with n-hexane. The extract was washed with water and dried. The solvent was removed by evaporation. The residual oily product was purified by silica gel column chromatography to obtain 3.1 g. of the desired oily product.

Workup

  1. temperatureThe resulting mixture was then refluxed for 1 hour
  2. additionThe reaction mixture was then poured into 50 ml
  3. extractionof water, and was then extracted with n-hexane
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was removed by evaporation
  7. customThe residual oily product was purified by silica gel column chromatography
  8. customto obtain 3.1 g

Sources & evidence

ORD record
ord-8615f1727909468eb7003a64771d6010
Source dataset
uspto-grants-1986_02
Patent number
US04571408

Reaction notes

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