Acetic Anhydride → HCID 54065749, compound

HRID 1578816Notes

Reaction equation

HRID 1578816 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:17])[CH2:10][CH2:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[CH:3][CH2:4][OH:5].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:17])[CH2:10][CH2:11][C:12](=[O:16])[CH:13]([CH3:14])[CH3:15])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54277596HCID 54277596, compound

Product 1

HCID 54065749HCID 54065749, compoundYield 94.7%

Procedure

To a solution of 3,7,11-trimethyl-2,6-dodecadien-10-on-1-ol (47.6 g) in acetic anhydride (61 g), pryidine (16 g) is added, and the resultant mixture is allowed to stand while cooling with ice for 3 hours. The reaction mixture is poured on ice and extracted with ether. The ether extract is washed with aqueous saturated solution of sodium chloride, aqueous solution of sodium hydrogen carbonate and water in order, dried over magnesium sulfate and evaporated to give 1-acetoxy-3,7,11-trimethyl-2,6-dodecadien-10-one (53 g) as an oil.

Workup

  1. temperaturewhile cooling with ice for 3 hours
  2. additionThe reaction mixture is poured on ice
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed with aqueous saturated solution of sodium chloride, aqueous solution of sodium hydrogen carbonate and water in order
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-a7f5cfce1e2142db8092dfdbd52434a9
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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