5-Chloro-9-isopropylidene-1,4-dihydro-1,4-methano-naphthalene → 5-Chloro-9-isopropylidene-1,2,3,4-tetrahydro-1,4-methano-naphthalene

HRID 39411Notes

Reaction equation

HRID 39411 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[C:12](=[C:13]([CH3:15])[CH3:14])[CH:7]2[CH:6]=[CH:5]1.[H][H]>[Pd].C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[C:12](=[C:13]([CH3:15])[CH3:14])[CH:7]2[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 578576065-Chloro-9-isopropylidene-1,4-dihydro-1,4-methano-naphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 674531575-Chloro-9-isopropylidene-1,2,3,4-tetrahydro-1,4-methano-naphthaleneYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

170 g of 5-Chloro-9-isopropylidene-1,4-dihydro-1,4-methano-naphthalene (0.785 mol), 0.5 g of Pd 10% (0.2 mmol) and 1 liter THF were charged in an hydrogenation reactor. 19 liter Hydrogen was feed at ambient temperature; the reaction was carried out at 0.05 MPa pressure. After complete conversion, the reaction mixture was filtered off over hyflo and product solution was evaporated to give 167 g product (Purity: 92%; Yield: 90%). The product was crystallized with MeOH, filtered off and dried. Purity: 97.54%

Workup

  1. customat ambient temperature
  2. filtrationAfter complete conversion, the reaction mixture was filtered off over hyflo and product solution
  3. customwas evaporated

Sources & evidence

ORD record
ord-3bbb27477eed4456bb3c94adb9b76beb
Source dataset
uspto-grants-2013_09
Patent number
US08524915B2

Reaction notes

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