Water → 1-(1-Naphthyl)-2-naphthol

HRID 1436334Notes

Reaction equation

HRID 1436334 reaction equation
C(O[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=C.[OH2:14]>CO>[C:12]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[CH:6][CH:5]=2)[C:11]([OH:14])=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

4

Reactant 2

HCID 962WaterHCID 12243312HCID 12243312, compound2×

Product 1

HCID 27552601-(1-Naphthyl)-2-naphtholYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

62.4 mg (0.20 mmol) of O-vinylnaphthol and 1.3 mg (0.002 mmol) of Co (OAc) (L3) were dissolved in 50 μl of methanol under the atmosphere, 18 μl (1.0 mmol) of water was added to the mixture, and the mixture was then stirred at −10° C. After 5 hours, the reaction solution was analyzed by HPLC, to find that 89% of the O-vinylnaphthol was left with an optical purity of 10% ee. Further, the reaction solution was purified by silica gel column chromatography to obtain the reaction product binaphthol in a yield of 11%. Also, the kre1 value showing the selectivity of reactions at this time was 11.0.

Workup

  1. additionwas added to the mixture
  2. waitwas left with an optical purity of 10% ee
  3. customFurther, the reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1fde794a262d4b84b604e800a14344df
Source dataset
uspto-grants-2009_11
Patent number
US07619003B2

Reaction notes

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