Hydrochloric Acid → HCID 67882429, compound

HRID 1086361Notes

Reaction equation

HRID 1086361 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:15])C(O)=O)=[CH:6][CH:5]=1.[Cl-].C([NH+]([CH2:22][CH3:23])CC)C.[I-].[K+].Br[CH2:27][CH2:28][CH2:29]CBr.Cl.[O:33]1CCCC1>>[C:11]([C:10]([C:7]1([CH:23]2[CH2:22][CH2:29][CH2:28][CH2:27]2)[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH2:8]1)=[O:33])([OH:15])=[O:1]

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 8028TetrahydrofuranHCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 1810716Benzenepropanoic acid, 4-Methyl-.alpha.-oxo-HCID 12698378Triethylazanium chloride

Product 1

HCID 67882429HCID 67882429, compoundYield 77%

Procedure

A 3N aqueous solution (5 ml) of sodium hydroxide and 10 ml of tetrahydrofuran were added to 0.89 g (5.0 mmoles) of p-methylphenylpyruvic acid, and the mixture was stirred until a completely uniform solution formed. Then, 50 mg of triethyl ammonium chloride, mg of potassium iodide and 0.7 ml (6 mmoles) of 1,4-dibromobutane were added, and the mixture reacted at room temperature for 48 hours. The reaction mixture was acidified with 1N hydrochloric acid and extracted with ether. The ether layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated. The NMR spectral analysis of the resulting oil to the determination that 1-carboxycarbonyl-p-methylphenylcyclopentane formed in a yield of 77 %.

Workup

  1. customformed
  2. customthe mixture reacted at room temperature for 48 hours
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over magnesium sulfate
  5. customThe drying reagent was separated by filtration
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b3ea94f89cfd40409238c420607be5ee
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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