Ethyl Acetate → 2,2'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene

HRID 1591356

Reaction equation

HRID 1591356 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[Br:22].C(OCC)(=O)C.[H][H]>[Ru].C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[Br:22]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 6199092,2'-Dibromo-1,1'-binaphthylHCID 178418361HCID 178418361, compound2×

Product 1

HCID 149427772,2'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthaleneYield 85.7%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Into a 500-ml stainless steel-made autoclave were introduced 35 g (0.085 mole) of 2,2'-dibromo-1,1'-binaphthyl (III), 5.25 g of 5%-ruthenium-on=carbon (manufactured by NECHEM CAT Inc.), 130 ml of ethyl acetate, and 130 ml of 95% ethanol. Hydrogenation was conducted at a hydrogen pressure of 50 kg/cm2 and a temperature of 100° C. for 20 hours, and it was then ascertained that the molar amount of hydrogen absorbed by the substrate had become four times that of the substrate. Thereafter, the reaction mixture was cooled to 30° C. and filtered to remove the catalyst. The resulting filtrate was allowed to stand at room temperature for a night, and crystals deposited were then collected by filtration. Thus, 30.6 g of the titled compound (IV) was obtained.

Workup

  1. customabsorbed by the substrate
  2. filtrationfiltered
  3. customto remove the catalyst
  4. waitto stand at room temperature for a night
  5. filtrationcrystals deposited were then collected by filtration

Sources & evidence

ORD record
ord-ebc3091b10114e6f9c5195ebe29ae605
Source dataset
uspto-grants-1993_04
Patent number
US05206399

Linked notes

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