Hydrochloric Acid → HCID 54298689, compound

HRID 1613504Notes

Reaction equation

HRID 1613504 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]=[C:7]1[CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2].Cl>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][C@@H:7]1[CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12682296HCID 12682296, compound

Product 1

HCID 54298689HCID 54298689, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Butyl-4-oxocyclohex-2-ene carboxylic acid ethyl ester [Tetrahedron 37 1033 (1981)] (4.48 g; 20 mmole) dissolved in absolute ethanol (15 ml) containing 2N hydrochloric acid (1 ml) was reduced at room temperature over 5% palladium on carbon (150 mg) at 50 p.s.i. (3.45 bar). After one hour the mixture was filtered through avicel and the solvent was evaporated under reduced pressure. The residue was taken up in diethyl ether and washed successively with water, saturated aqueous sodium bicarbonate and water. Drying over MgSO4 and evaporation gave an oil (4.2 g) which was chromatographed on silica. Elution with diethyl ether:hexane (2:8) gave the pure title ester (3.6 g, 80%) as a clear liquid. Found: C,68.86; H,9.84. C13H22O3 requires C,68.99; H,9.80%.

Workup

  1. filtrationAfter one hour the mixture was filtered through avicel
  2. customthe solvent was evaporated under reduced pressure
  3. washwashed successively with water, saturated aqueous sodium bicarbonate and water
  4. dry with materialDrying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-a5a7028d4e274ffe8db54dcee0e896d9
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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