Ethanol → Indane

HRID 1770185Notes

Reaction equation

HRID 1770185 reaction equation
C([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)CCCCCCC.BrC1C=C2C(=CC=1)CC(CCCCCCCC)C2.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 220990862-Octylindane-5-boronic acidHCID 235091535-Bromo-2-octylindan

Product 1

HCID 10326IndaneYield 83%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

Then, 0.89 g (3.2 mM) of 2-octylindan-5-boronic acid, 1.00 g (3.2 mM) of 5-bromo-2-octylindan, 2 ml of ethanol, 4 ml of benzene, 4 ml of 2M-sodium carbonate aqueous solution and 0.12 g of tetrakis(triphenylphosphine)palladium (O) were mixed and heat-refluxed for 1.5 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 1.22 g (2.66 mM) of 5,5'-bi-2-octyl)indan (Yield: 83%). ##STR320##

Workup

  1. temperatureheat-refluxed for 1.5 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. custompurified by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-468f604d477e4bd9a81199d3742c75bb
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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