Acetic Anhydride → (Z,Z)-11,13-Hexadecadienal

HRID 903497

Reaction equation

HRID 903497 reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]/[CH2:15][CH3:16].C(OC(=O)C)(=O)C>N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]/[CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 536556311,13-Hexadecadien-1-ol, (11Z,13Z)-

Product 1

HCID 6436739(Z,Z)-11,13-Hexadecadienal

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(11Z,13Z)-11,13-hexadecadien-1-ol (3.19 mmol) and acetic anhydride (6.38 mmol), in 5 ml of dry pyridine, are stirred under nitrogen at room temperature for 20 hours. The reaction mixture is then poured in sodium bicarbonate solution and extracted with pentane (2X). The organic layer is washed with dilute HCl and with brine, dried over magnesium sulfate and the solvent removed in vacuo. The crude product is purified to yield the final product, (11Z,13Z)-11,13-hexadecadien-1-al.

Workup

  1. extractionextracted with pentane (2X)
  2. washThe organic layer is washed with dilute HCl and with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed in vacuo
  5. customThe crude product is purified

Sources & evidence

ORD record
ord-904733ac283b49fcabdacd2e6817bb08
Source dataset
uspto-grants-1980_10
Patent number
US04228093

Linked notes

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