HCID 53755082, compound → HCID 14257704, compound

HRID 867989Notes

Reaction equation

HRID 867989 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[CH:14][CH2:15][CH3:16])[C:9]2=[O:13])=[CH:4][C:3]=1[O:17][CH3:18]>CC(O)C.[Pd]>[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:14][CH2:15][CH3:16])[C:9]2=[O:13])=[CH:4][C:3]=1[O:17][CH3:18]

Participants

4

Reactant 1

HCID 53755082HCID 53755082, compound

Product 1

HCID 14257704HCID 14257704, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

7,8-Dichloro-6-methoxy-2-propylidene-1-tetralone (1.1 g) in 50 ml of 2-propanol and 150 mg of 5% Pd/C catalyst, were placed in a Parr apparatus and hydrogenated at 30 psi for 20 minutes. The reaction mixture was warmed slightly, the catalyst filtered, rinsed with 2-propanol, evaporated to dryness and chromatographed on 40 g SiO2 (ethyl acetae-hexane, 1:3) to yield 680 mg of 7,8-dichloro-6-methoxy-2-propyl-1-tetralone which melted at 127°-9° C. after recrystallization from ethyl acetate.

Workup

  1. temperatureThe reaction mixture was warmed slightly
  2. filtrationthe catalyst filtered
  3. washrinsed with 2-propanol
  4. customevaporated to dryness
  5. customchromatographed on 40 g SiO2 (ethyl acetae-hexane, 1:3)

Sources & evidence

ORD record
ord-e24a83bc302447f595ef1c2642a44fca
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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