Acetic Anhydride → HCID 67199459, compound

HRID 551668Notes

Reaction equation

HRID 551668 reaction equation
O[CH:2]([CH2:8][CH2:9][CH:10]=[CH2:11])[CH:3]([CH3:7])[C:4]([OH:6])=O.C([O-])(=O)C.[K+].C(OC(=O)C)(=O)C>C(OCC)(=O)C>[CH3:7][C@@:3]12[C:4](=[O:6])[CH2:11][C@@H:10]1[CH2:9][CH:8]=[CH:2]2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 14924162HCID 14924162, compound

Product 1

HCID 67199459HCID 67199459, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 3-hydroxy-2-methylhept-6-enoic acid (5.45 g, 34.5 mmol), potassium acetate (7.0 g, 71.3 mmol), and acetic anhydride (30 mL) was stirred at room temperature for 1.5 hours and then stirred for 3 hours under conditions of heating to reflux. The reaction solution was left overnight, then diluted with ethyl acetate, washed with water, saturated aqueous sodium bicarbonate, and saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain the compound of interest as a pale yellow oil (810 mg).

Workup

  1. temperatureof heating to reflux
  2. waitThe reaction solution was left overnight
  3. washwashed with water, saturated aqueous sodium bicarbonate, and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b70956e1f8d4004a6c914cdc674b12a
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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