Acetic Anhydride → 1,3-Hexadien-1-ol acetate

HRID 482825Notes

Reaction equation

HRID 482825 reaction equation
[CH:1](=[O:7])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6].[C:8]([O:11]C(=O)C)(=[O:10])[CH3:9].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH:1]([OH:7])=[CH:2][CH:3]=[CH:4][CH2:5][CH3:6].[C:8]([O-:11])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 5281168trans-2-Hexenal

Product 1

HCID 1317145341,3-Hexadien-1-ol acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of trans-2-hexenal (84.4 g; 0.86 mol) and acetic anhydride (102 g, 1 mol), 8 g (0.065 mol) of 4-dimethylaminopyridine and 105 g (1.04 mol) of triethylamine are added. The mixture is heated to 80° C. for two hours and then, after cooling at room temperature, 200 ml of chloroform is added. The organic layer is washed with two portions of 100 ml of ice-water and then with 30 ml of aqueous sodium bicarbonate. The chloroform layer is dried over MgSO4. Evaporation of the solvent under vacuum yields a residue which is distilled at 80° C./60 mmHg. Yield 106 g. N.M.R. and I.R. Spectrum confirm the assigned structure. The product is a mixture of four isomers containing more than 65% of the Δ-3,4-(E)-isomers.

Workup

  1. additionare added
  2. temperatureafter cooling at room temperature
  3. washThe organic layer is washed with two portions of 100 ml of ice-water
  4. dry with materialThe chloroform layer is dried over MgSO4
  5. customEvaporation of the solvent under vacuum
  6. customyields a residue which
  7. distillationis distilled at 80° C./60 mmHg
  8. additiona mixture of four isomers
  9. additioncontaining more than 65% of the Δ-3,4-(E)-isomers

Sources & evidence

ORD record
ord-f17d0e47f5ce42aabe9451e7c8306033
Source dataset
uspto-grants-1986_03
Patent number
US04576746

Reaction notes

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