Acetic Anhydride → (E,E)-1-acetoxy-4-ethyl-2,4-heptadiene

HRID 2295016Notes

Reaction equation

HRID 2295016 reaction equation
[CH2:1](/[C:3](=[CH:8]\[CH2:9][CH3:10])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].[C:11](OC(=O)C)(=[O:13])[CH3:12]>N1C=CC=CC=1>[C:11]([O:7][CH2:6]/[CH:5]=[CH:4]/[C:3](/[CH2:1][CH3:2])=[CH:8]/[CH2:9][CH3:10])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86749298(E,E)-4-ethyl-2,4-heptadien-1-ol

Product 1

HCID 86749299(E,E)-1-acetoxy-4-ethyl-2,4-heptadieneYield 74.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (E,E)-4-ethyl-2,4-heptadien-1-ol (10.1 g) in pyridine (29 g) at 0° C. was added dropwise acetic anhydride (22.2 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 chromatographed on silica gel (5% ethyl acetate in hexane) to give (E,E)-1-acetoxy-4-ethyl-2,4-heptadiene (9.75 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. customThe residue was chromatographed on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-442d74d91b0346fcb231f3e075946fd2
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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