Perchloric Acid → HCID 20367014, compound

HRID 616971Notes

Reaction equation

HRID 616971 reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11](=O)[C:10]2[CH:9]=[C:8]([CH2:14][C:15]([OH:17])=[O:16])[CH:7]=[CH:6][C:5]=2[CH2:4]1)[CH3:2].[H][H].Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[CH2:1]([CH:3]1[CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([CH2:14][C:15]([OH:17])=[O:16])[CH:7]=[CH:6][C:5]=2[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 20367020HCID 20367020, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20367014HCID 20367014, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5.4 g of 6-ethyl-5,6,7,8-tetrahydro-8-oxo-naphthalene-2-acetic acid are dissolved in 150 cc of acetic acid and hydrogenation is effected at 4 atmospheres of hydrogen pressure and 45° with the addition of 1 g of palladium/charcoal (10%) and 2 cc of 70% aqueous perchloric acid. After the take up of the calculated amount of hydrogen, filtration is effected, 2 g of sodium acetate are added and the solution is concentrated. The residue is divided between ether and water, the ether extract is dried over sodium sulphate and concentrated by evaporation. The resulting 6-ethyl-5,6,7,8-tetrahydronaphthalene-2-acetic acid is recrystallized from hexane and has a M.P. of 64°-66°.

Workup

  1. filtrationAfter the take up of the calculated amount of hydrogen, filtration
  2. addition2 g of sodium acetate are added
  3. concentrationthe solution is concentrated
  4. extractionthe ether extract
  5. dry with materialis dried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. customThe resulting 6-ethyl-5,6,7,8-tetrahydronaphthalene-2-acetic acid is recrystallized from hexane

Sources & evidence

ORD record
ord-39d5318ed1f8414b824053a52e1dd418
Source dataset
uspto-grants-1978_02
Patent number
US04076838

Reaction notes

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