Acetic Anhydride → HCID 20355562, compound

HRID 371652Notes

Reaction equation

HRID 371652 reaction equation
[Mg].[CH:2](Br)=[CH2:3].[CH2:5]([O:12][CH2:13][CH:14]=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>O1CCCC1>[CH2:5]([O:12][CH2:13][CH:14]([O:15][C:16](=[O:18])[CH3:17])[CH:2]=[CH2:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 11641BromoetheneHCID 108989(Phenylmethoxy)acetaldehydeHCID 5462224Magnesium

Product 1

HCID 20355562HCID 20355562, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Magnesium metal (5 g., 0.206 mole) is suspended in tetrahydrofuran (100 ml.) in a three-necked, round-bottomed flask protected by a dry ice condenser and equipped with a mechanical stirrer. The stirrer is started and vinyl bromide (22 g., 0.206 mole) in tetrahydrofuran is added at such a rate as to keep the solvent refluxing. The reaction mixture is refluxed for 0.5 hours after the addition is complete. The reaction mixture is then cooled to 0°-5° C. and benzyloxyacetaldehyde (24 g., 0.16 mole) in tetrahydrofuran (15 ml.) is added dropwise. After 1.5 hours at 0°-5° C., there is added acetic anhydride (26 g., 0.255 mole) and the reaction mixture is allowed to come to room temperature. After 20 hours at room temperature, ice water (500 ml.) is added and the product is extracted into ethyl acetate (3 × 100 ml.). The ethyl acetate extract is washed with brine, dried (Na2SO4), and distilled. There is obtained 17 g. (49%) of the title compound, b.p. 85°-95° C./0.05 mm.

Workup

  1. customprotected by a dry ice condenser
  2. customequipped with a mechanical stirrer
  3. temperaturerefluxing
  4. temperatureThe reaction mixture is refluxed for 0.5 hours
  5. additionafter the addition
  6. temperatureThe reaction mixture is then cooled to 0°-5° C.
  7. customto come to room temperature
  8. waitAfter 20 hours at room temperature
  9. extractionthe product is extracted into ethyl acetate (3 × 100 ml.)
  10. extractionThe ethyl acetate extract
  11. washis washed with brine
  12. dry with materialdried (Na2SO4)
  13. distillationdistilled
  14. customThere is obtained 17 g

Sources & evidence

ORD record
ord-59e1b5590e544819943c0a79f7451506
Source dataset
uspto-grants-1978_05
Patent number
US04087435

Reaction notes

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