Hydrochloric Acid → HCID 23679673, compound

HRID 1086360Notes

Reaction equation

HRID 1086360 reaction equation
[OH-].[Na+:2].[I-].[K+].[C:5]1([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[O:16]=[C:12]([CH:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:22][C:21]1[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=1)[C:13]([O-:15])=[O:14].[Na+:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 997Phenylpyruvic acidHCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium Hydroxide2×

Product 1

HCID 23679673HCID 23679673, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous solution (4 ml) of sodium hydroxide, 10 ml of tetrahydrofuran, 100 mg of potassium iodide and 100 mg of triethylbenzylammonium chloride were added to 0.83 g (5.0 mmoles) of phenylpyruvic acid to form a solution. Then, 0.8 ml of p-chlorobenzyl chloride was added, and the mixture was stirred at room temperature for 36 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with 100 ml of ether. The ether layer was dried over magnesium sulfate and concentrated under reduced pressure to give a pale yellowish white oil. A 1N aqueous solution of sodium hydroxide was added to the product, and the mixture was concentrated under reduced pressure. Ether was added to the resulting semi-soid mixture, and the precipitated sodium 2-oxo-3-phenyl-4-(p-chlorophenyl)butanoate was isolated by filtration as a white solid (yield 37 %).

Workup

  1. customto form a solution
  2. extractionextracted with 100 ml of ether
  3. dry with materialThe ether layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a pale yellowish white oil
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionEther was added to the resulting semi-soid mixture

Sources & evidence

ORD record
ord-20b32441346c4da29d776d638bb5c09c
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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