Hydrochloric Acid → HCID 67332216, compound

HRID 840978Notes

Reaction equation

HRID 840978 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])=O.Cl.O1C[CH2:21][CH2:20][CH2:19]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:10](=[CH:1][C:2]1[CH:5]=[CH:21][CH:20]=[CH:19][CH:3]=1)[CH2:9][CH2:8][C:7]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10883Ethyl levulinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67332216HCID 67332216, compound

Reagents, catalysts & solvents 1

HCID 70671Benzyltriphenylphosphonium chlorideCatalyst

Procedure

Benzyltriphenylphosphonium chloride (29.67 g, 76.30 mmol) was added to a solution of potassium tertbutoxide (9.34 g, 83.24 mmol) in tetrahydrofuran (300 ml), followed by stirring at room temperature for 3 hours, and ethyl levulinate (10.00 g, 69.36 mmol) was added dropwise thereto. The reaction mixture was stirred at room temperature for 2 hours and then heated under reflux for another 2 hours. The reaction mixture was adjusted to pH 1 with a 1N-aqueous hydrochloric acid solution and extracted with ethyl acetate, and the extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/25) to obtain 9.20 g of ethyl 4-methyl-5-phenyl-4-pentenoate.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. temperatureheated
  3. temperatureunder reflux for another 2 hours
  4. extractionextracted with ethyl acetate
  5. washthe extract solution was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/25)

Sources & evidence

ORD record
ord-6aa584d5159a436e9680eb2e732dfbbf
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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