Acetic Anhydride → HCID 10931553, compound

HRID 1954435Notes

Reaction equation

HRID 1954435 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH3:6][O:7][CH:8]([CH:11]=[CH2:12])[CH2:9]O.C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:9][CH:8]([O:7][CH3:6])[CH:11]=[CH2:12])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic Anhydride2×HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 27350782-METHOXY-3-BUTEN-1-OL

Product 1

HCID 10931553HCID 10931553, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In a 3-liter, 3-necked round bottom flask equipped with a mechanical stirrer, nitrogen inlet, temperature probe and vigoreux column was placed 1200 mL toluene, sodium acetate (88.59 g, 1.08 mol) and 2-methoxy-3-buten-1-ol (250.0 g, 2.45 mol). Mixture heated to 60° C. with stirring. Once temperature had stabilized, acetic anhydride (288.83 g, 2.80 mol) added dropwise over 2.5 hours. Maintained temperature for 1.5 hrs then increased temperature to 70° C. for 1 hour. Gas chromatography showed no trace of starting material in reaction. Began cooling reaction to room temperature. When reaction had cooled to 38° C., one liter of a 5% sodium bicarbonate solution was added at high speed to decompose any excess acetic anhydride remaining in the reaction. Extracted reaction twice with water, layers separated, the aqueous layer extracted twice with toluene and added to the organic layer. Organic layer dried with anhydrous magnesium sulfate, filtered and concentrated by rotovap. Yield 222.43 g (63.0%) of a clear, colorless material. 1H NMR consistent with 1-acetoxy-2-methoxy butene.

Workup

  1. customIn a 3-liter, 3-necked round bottom flask equipped with a mechanical stirrer, nitrogen inlet
  2. temperatureMaintained temperature for 1.5 hrs
  3. temperaturethen increased temperature to 70° C. for 1 hour
  4. customin reaction
  5. temperatureBegan cooling
  6. customreaction to room temperature
  7. customWhen reaction
  8. temperaturehad cooled to 38° C.
  9. customin the reaction
  10. extractionExtracted
  11. customreaction twice with water, layers
  12. customseparated
  13. extractionthe aqueous layer extracted twice with toluene
  14. additionadded to the organic layer
  15. dry with materialOrganic layer dried with anhydrous magnesium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated by rotovap

Sources & evidence

ORD record
ord-dbbd12d93bba4fa7b05c3083e5032c7b
Source dataset
uspto-grants-2000_09
Patent number
US06121399

Reaction notes

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