2-Naphthol → Binol

HRID 1799355Notes

Reaction equation

HRID 1799355 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11]>O>[OH:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]=1[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11]

Participants

3

Reactant 1

HCID 86632-Naphthol

Product 1

HCID 11762Binol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g 2-naphthol, 11.4 g FeCl3.6H2O and 100 ml water are added to a 200 ml flask in order to perform stirring reaction in 65° C. water bath, TLC (thin layer chromatography) is adopted for tracking, the reaction product is filtered 3 hours after the reaction to obtain the solid 2,2′-dihydroxy-1,1′-binaphthyl, the 2,2′-dihydroxy-1,1′-binaphthyl is washed with 50 ml water, the washing solution is incorporated into the filtrate, 7.5 ml H2O2 with the concentration of 30% is slowly and dropwise added to the filtrate under stirring, the filtrate is continuously stirred for 10 minutes, 2 g 2-naphthol is added to perform stirring reaction at 65° C., TLC tracking is performed until the reaction comes to an end, and the reaction product is filtered to obtain the solid 2,2′-dihydroxy-1,1′-binaphthyl. The above steps are repeated so as to lead to the results in Table 6. The HPLC analysis result of the eleventh circular reaction product shows that the conversion rate of the 2-naphthol is more than 98%, and the selectivity of the 2,2′-dihydroxy-1,1′-binaphthyl is more than 99%.

Workup

  1. customreaction in 65° C. water bath
  2. filtrationthe reaction product is filtered 3 hours
  3. customafter the reaction

Sources & evidence

ORD record
ord-e823668a4a2e4edea031bdc105f26be3
Source dataset
uspto-grants-2013_01
Patent number
US08344080B2

Reaction notes

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