Hydrochloric Acid → HCID 21256662, compound

HRID 635828Notes

Reaction equation

HRID 635828 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]2[CH2:18][CH:17]=[CH:16][CH2:15][C:14]2=[O:19])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].Cl>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21256660HCID 21256660, compound

Product 1

HCID 21256662HCID 21256662, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10.2 g of 2-(3,4-diethoxyphenyl)cyclohex-4-enone in 600 ml of tetrahydrofuran are admixed with 1.5 ml of conc. hydrochloric acid and 400 mg of 10% palladium on carbon and hydrogenated. The catalyst is filtered off, the solution is concentrated under reduced pressure and the residue is chromatographed over silica gel using a mixture of petroleum ether/ethyl acetate in a ratio of 2/1. Concentration of the appropriate eluate fractions gives 8.25 g (80.9% of Th.) of the title compound as an oil which solidifies.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution is concentrated under reduced pressure
  3. customthe residue is chromatographed over silica gel using
  4. additiona mixture of petroleum ether/ethyl acetate in a ratio of 2/1

Sources & evidence

ORD record
ord-f77f4ea0c6ab4145aa19470253100c1a
Source dataset
uspto-grants-2001_02
Patent number
US06191138B1

Reaction notes

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