Acetyl chloride → 2-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

HRID 1947230Notes

Reaction equation

HRID 1947230 reaction equation
[H-].[Na+].[CH2:3]1COC[CH2:4]1.[OH:8][C:9]1[C:14](/[CH:15]=[CH:16]/[CH3:17])=[CH:13][CH:12]=[CH:11][C:10]=1[C:18](=[O:20])[CH3:19].C(Cl)(=O)C>O>[CH3:3][C:4]1[O:8][C:9]2[C:10]([C:18](=[O:20])[CH:19]=1)=[CH:11][CH:12]=[CH:13][C:14]=2/[CH:15]=[CH:16]/[CH3:17]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 110084541-{2-Hydroxy-3-[(1E)-prop-1-en-1-yl]phenyl}ethanone

Product 1

HCID 574388872-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.52 g (313.2 mmol) of 60% sodium hydride (suspension in mineral oil) are introduced into 300 ml of absolute THF under argon at 10° C. 18.4 g (104.4 mmol) of 1-{2-hydroxy-3-[(1E)-prop-1-en-1-yl]phenyl}ethanone are slowly added dropwise to the suspension. After 15 min, 9 g (114.9 mmol) of acetyl chloride are added. The reaction mixture is stirred at room temperature ovemight. Hydrolysis is carried out with 300 ml of water, and the mixture is extracted several times with ethyl acetate. Washing of the organic phase with saturated sodium chloride solution is followed by drying over sodium sulfate. The solvent is then removed in vacuo. The residue is taken up in 200 ml of methanol and heated with 50 ml of 20% strength hydrochloric acid at 80° C. for 30 min. The solvent is then removed in vacuo, and the residue is mixed with 400 ml of water. Several extractions with dichloromethane are carried out. After the organic phase has been dried over magnesium sulfate, the solvent is removed in vacuo and the residue is purified by column chromatography (mobile phase: dichloromethane/methanol 98:2). 10.5 g (50.2% of theory) of the title compound are obtained as a yellow oil.

Workup

  1. customHydrolysis
  2. extractionthe mixture is extracted several times with ethyl acetate
  3. washWashing of the organic phase with saturated sodium chloride solution
  4. dry with materialby drying over sodium sulfate
  5. customThe solvent is then removed in vacuo
  6. temperatureheated with 50 ml of 20% strength hydrochloric acid at 80° C. for 30 min
  7. customThe solvent is then removed in vacuo
  8. additionthe residue is mixed with 400 ml of water
  9. extractionSeveral extractions with dichloromethane
  10. dry with materialAfter the organic phase has been dried over magnesium sulfate
  11. customthe solvent is removed in vacuo
  12. customthe residue is purified by column chromatography (mobile phase: dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-36c6357b5bee4f78bf8f3d6b0d99edf8
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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