Hydrochloric Acid → HCID 15024005, compound

HRID 1086354Notes

Reaction equation

HRID 1086354 reaction equation
[OH-].[Na+].[C:3]1([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15](Br)[CH:16]=[C:17]([CH3:19])[CH3:18].Cl>>[O:14]=[C:10]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 997Phenylpyruvic acidHCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 15024005HCID 15024005, compound

Procedure

A 1N aqueous solution of sodium hydroxide (20 ml: 20 mmoles) was added to 1.64 g (10 mmoles) of phenylpyruvic acid to form a solution. Then 1.49 g (10 mmoles) of prenyl bromide was added, and the mixture was reacted at room temperature for 13 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with three 50 ml portions of the ether. The organic layers were dried over magnesium sulfate, and the ether was evaporated under reduced pressure to give 2-oxo-3-phenyl-6-methyl-5-heptenoic acid as a pale yellowish white solid. The product was converted to a methyl ester using diazomethane, and the methyl ester was purified by silica gel column chromatography to give methyl 2-oxo-3-phenyl-6-methyl-5-heptenoate as a nearly pure product (1.72 g; yield 70 %).

Workup

  1. customto form a solution
  2. customthe mixture was reacted at room temperature for 13 hours
  3. extractionextracted with three 50 ml portions of the ether
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. customthe ether was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7ba5279902f14ce098e149cafea22bca
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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