Toluene → 2,2'-Dimethoxy-1,1'-binaphthalene

HRID 1799357Notes

Reaction equation

HRID 1799357 reaction equation
O[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]=1O.[OH-:23].[Na+].S([O:30][CH3:31])(OC)(=O)=O.[CH3:32]C1C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:32][O:23][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[O:30][CH3:31]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 11762BinolHCID 14798Sodium Hydroxide

Product 1

HCID 2356162,2'-Dimethoxy-1,1'-binaphthalene

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

14.3 g 2,2′-Dihydroxy-1,1′-binaphthyl prepared in the step a) of the Example 19, 40 ml sodium hydroxide with the concentration of 7.5%, 0.5 g tetrabutylammonium hydrogen sulfate and 40 ml methylbenzene are added to a round bottom flask with the volume of 100 mL. 16.4 g dimethyl sulfate is dropwise added to the round bottom flask to perform stirring reaction at 70° C.; and after the reaction is performed for 4 hours, the reaction product is filtered to obtain 2,2′-dimethoxy-1,1′-binaphthyl. The methylbenzene is separated from the filtrate. The aforementioned reaction is repeated, and recycling of the methylbenzene five times leads to the results in Table 7.

Workup

  1. additionare added to a round bottom flask with the volume of 100 mL
  2. customreaction at 70° C.
  3. filtrationthe reaction product is filtered

Sources & evidence

ORD record
ord-a001cbe75c8e4e9b91c4ce9c16498b8d
Source dataset
uspto-grants-2013_01
Patent number
US08344080B2

Reaction notes

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