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

HRID 1799356Notes

Reaction equation

HRID 1799356 reaction equation
[OH-:1].[Na+].O[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1O.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:1][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=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

Conditions

Temperature
70 °C

Procedure

52 g NaOH with the concentration of 30% is formulated at room temperature. Under stirring, 143 g 2,2′-dihydroxy-1,1′-binaphthyl prepared according to the above method, 5.2 g tetrabutylammonium hydrogen sulfate and 500 ml methylbenzene are heated up to 70° C. while being dropwise added with 164 g dimethyl sulfate in order to perform stirring reaction, which is followed by TLC tracing, and upon the disappearance of monoether spots, the reaction continues for a while. The reaction product is cooled and filtered, the filter cake is washed sequentially with 400 ml methylbenzene and 400 ml NaOH solution with the concentration of 5%, then washed with water to be neutral and finally dried to obtain the 2,2′-dimethoxy-1,1′-binaphthyl. The HPLC analysis result shows that the conversion rate of the 2,2′-dihydroxy-1,1′-binaphthyl is more than 99%, the purity of the 2,2′-dimethoxy-1,1′-binaphthyl is more than 98% and the yield of the 2,2′-dimethoxy-1,1′-binaphthyl is more than 95%. Methylbenzene layers are merged to separate out the methylbenzene for recycling.

Workup

  1. customis formulated at room temperature
  2. stirringto perform stirring
  3. customreaction, which
  4. temperatureThe reaction product is cooled
  5. filtrationfiltered
  6. washthe filter cake is washed sequentially with 400 ml methylbenzene and 400 ml NaOH solution with the concentration of 5%
  7. washwashed with water
  8. customfinally dried

Sources & evidence

ORD record
ord-8a2142957ee743b5b79b56efa1ab5ff3
Source dataset
uspto-grants-2013_01
Patent number
US08344080B2

Reaction notes

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