Boron trifluoride etherate → 1,1'-Binaphthalene, 4,4'-dimethoxy-

HRID 1955293Notes

Reaction equation

HRID 1955293 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.B(F)(F)F.C[CH2:18][O:19][CH2:20][CH3:21]>C(#N)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:3]2[C:4]3[C:21](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:20]([O:19][CH3:18])=[CH:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 166681-Methoxynaphthalene

Product 1

HCID 118231841,1'-Binaphthalene, 4,4'-dimethoxy-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In synthetic route `A3`, 1-methoxynaphthalene and a solution of tris(trifluoroacetato)thallium[III] in acetonitrile are charged to a reaction vessel. Boron trifluoride etherate is added and the reaction mixture stirred at room temperature for between approximately 1-2 h to provide the intermediate 4,4'-dimethoxy-1,1'-binaphthyl. The 4,4'-dimethoxy-1,1'-binaphthyl intermediate is subsequently demethylated using boron tribromide (BBr3) which is added slowly to a dichloromethane solution of the intermediate to maintain the temperature at about -78° C. The reaction mixture is then warmed to room temperature and stirred for approximately 16 h in an inert atmosphere, then poured into water. The white crystals that form are 4,4'-Dihydroxy-1,1'-binaphthyl.

Sources & evidence

ORD record
ord-3a5cabf6b9484581b0eb7500c3280a1e
Source dataset
uspto-grants-2000_09
Patent number
US06124421

Reaction notes

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