Hydrochloric Acid → HCID 15023975, compound

HRID 1086347Notes

Reaction equation

HRID 1086347 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].[CH:16](I)([CH3:18])[CH3:17].Cl>CO>[O:13]=[C:9]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:16]([CH3:18])[CH3:17])[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 5805353-(4-Chlorophenyl)-2-oxopropanoic acid

Product 1

HCID 15023975HCID 15023975, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

p-Chlorophenylpyruvic acid (1.98 g, 10.0 mmoles) was dissolved in 20 ml of methanol, and a 3N aqueous solution of sodium hydroxide (8.0 ml, 24 mmoles) was added to form a solution. Then, 2.0 ml of isopropyl iodide was added, and the mixture was stirred at 35° C. for 36 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with three 30 ml portions of ether. The ether layers were dried over magnesium sulfate and concentrated under reduced pressure. The resulting pale yellowish white oil was purified by silica gel column chromatography (ethyl acetate:hexane=1:7) to obtain pure 2-oxo-3-(p-chlorophenyl)-4-methylpentanoic acid as an oil in a yield of 48 %. This product was treated with an aqueous solution of sodium hydroxide, and isolated as a pure sodium salt.

Workup

  1. customto form a solution
  2. extractionextracted with three 30 ml portions of ether
  3. dry with materialThe ether layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting pale yellowish white oil was purified by silica gel column chromatography (ethyl acetate:hexane=1:7)

Sources & evidence

ORD record
ord-8b7197c0ab3b4c6ea5b9974ef3b2ca38
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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