Acetic Anhydride → HCID 86749301, compound

HRID 2396921Notes

Reaction equation

HRID 2396921 reaction equation
[CH3:1]/[C:2](=[CH:7]\[CH2:8][CH3:9])/[CH:3]=[CH:4]/[CH2:5][OH:6].[C:10](OC(=O)C)(=[O:12])[CH3:11]>N1C=CC=CC=1>[C:10]([O:6][CH2:5]/[CH:4]=[CH:3]/[C:2](/[CH3:1])=[CH:7]/[CH2:8][CH3:9])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10654230HCID 10654230, compound

Product 1

HCID 86749301HCID 86749301, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (E,E)-4-methyl-2,4-heptadien-1-ol (106 g) in pyridine (333 g) at 0° C. was added dropwise acetic anhydride (258 g). After two hours at room temperature, the reaction mixture was evaporated in vacuo. The residue was diluted with ethyl acetate, washed with 0.5N-hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was distilled to give (E,E)-1-acetoxy-4-methyl-2,4-heptadiene (117.65 g) as an oil.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 0.5N-hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-52d3c975928e41f5a18b7e1948627a6d
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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