Acetic Anhydride → HCID 86749296, compound

HRID 2295007Notes

Reaction equation

HRID 2295007 reaction equation
[CH2:1](/[C:3](=[CH:8]\[CH:9]([CH3:11])[CH3:10])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1.ClCCl>[C:12]([O:7][CH2:6]/[CH:5]=[CH:4]/[C:3](/[CH2:1][CH3:2])=[CH:8]/[CH:9]([CH3:10])[CH3:11])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86749297HCID 86749297, compound

Product 1

HCID 86749296HCID 86749296, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E,E)-4-ethyl-6-methyl-2,4-heptadien-1-ol (23.8 g) in pyridine (61.4 g) at 0° C. was added dropwise acetic anhydride (50.9 g). After two hours, the reaction mixture was diluted with dichloromethane. The solution was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (3% ethyl acetate-hexane) to give (E,E)-1-acetoxy-4-ethyl-6-methyl-2,4-heptadiene (24.11 g) as an oil.

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (3% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9e0f3dafff99435fa5f9b864ca9a80d6
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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