HCID 19433143, compound → 4-Oxo-6-phenylhex-2-ynoic acid

HRID 326350Notes

Reaction equation

HRID 326350 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]#[C:17][C:18]([OH:20])=[O:19]>S(=O)(=O)(O)O.CC(C)=O>[O:14]=[C:15]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:16]#[C:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 19433143HCID 19433143, compoundHCID 131709961Jones' reagent

Product 1

HCID 194331524-Oxo-6-phenylhex-2-ynoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of Jones Reagent (a 2.67M solution in sulphuric acid; 2.07 ml, 5.5 mmol) was added dropwise to a solution of 4-hydroxy-6-phenylhex-2-ynoic acid (750 mg, 3.7 mmol) in acetone (12 ml) at 0° and the reaction mixture was maintained at 0° for 70 minutes. The mixture was quenched with ethanol (2 ml) and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave the title acid as a yellow oil which was used directly in the next step.

Workup

  1. temperaturethe reaction mixture was maintained at 0° for 70 minutes
  2. customThe mixture was quenched with ethanol (2 ml)
  3. extractionextracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulphate)

Sources & evidence

ORD record
ord-1e41589a7b2f474ca3b1c6d9fcb6f97b
Source dataset
uspto-grants-1993_12
Patent number
US05268387

Reaction notes

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