Hydrochloric Acid → [2,2'-Binaphthalen]-6-ol

HRID 2384518Notes

Reaction equation

HRID 2384518 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:21]1[C:22]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:20]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 58876221[2,2'-Binaphthalen]-6-olYield 48.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a three-necked flask were placed 26.8 g of 6-bromo-2-naphthol, 4.6 g of tetrakistriphenylphosphinepalladium and 100 ml of toluene and the mixture was stirred at 50° C. When the solids nearly dissolved, a solution of 20.6 g of 2-naphthaleneboronic acid in 100 ml of ethanol was added and stirred. When the solutions mixed with each other, a solution of 30 g of sodium carbonate in 100 ml of water was added, the mixture was heated to the reflux temperature and stirred for 1 hour. Upon completion of the reaction, dilute hydrochloric acid was added until the aqueous layer became weakly acidic, the organic layer was recovered and the solvent was distilled off under reduced pressure. The crude product was recrystallized from a mixture of toluene and ethyl acetate, the crystals were collected by filtration, washed with toluene and dried at 80° C. under reduced pressure to give 15.6 g of 6-(2-naphthyl)-2-naphthol. The unreacted 6-bromo-2-naphthol was not detected.

Workup

  1. customIn a three-necked flask were placed
  2. dissolutionWhen the solids nearly dissolved
  3. additionwas added
  4. temperaturethe mixture was heated to the reflux temperature
  5. stirringstirred for 1 hour
  6. additionwas added until the aqueous layer
  7. customthe organic layer was recovered
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was recrystallized from a mixture of toluene and ethyl acetate
  10. filtrationthe crystals were collected by filtration
  11. washwashed with toluene
  12. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-7bf60525710040d691bab91ca24fdb8b
Source dataset
uspto-grants-2012_09
Patent number
US08263770B2

Reaction notes

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