Hydrochloric Acid → 6-Phenylnaphthalen-2-ol

HRID 2384515Notes

Reaction equation

HRID 2384515 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.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.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>[C:13]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 66827Phenylboronic Acid

Product 1

HCID 101251826-Phenylnaphthalen-2-olYield 45.1%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
50 °C

Procedure

In a three-necked flask equipped with a condenser, a thermometer and a stirrer 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 14.6 g of phenylboronic 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 50 ml of toluene and the crystals collected by filtration were washed with toluene and dried at 80° C. under reduced pressure to give 11.9 g of 6-phenyl-2-naphthol. The unreacted 6-bromo-2-naphthol was not detected by HPLC.

Workup

  1. customIn a three-necked flask equipped with a condenser
  2. dissolutionWhen the solids nearly dissolved
  3. stirringstirred
  4. additionwas added
  5. temperaturethe mixture was heated to the reflux temperature
  6. stirringstirred for 1 hour
  7. additionwas added until the aqueous layer
  8. customthe organic layer was recovered
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe crude product was recrystallized from 50 ml of toluene
  11. filtrationthe crystals collected by filtration
  12. washwere washed with toluene
  13. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-1f727734ad3340c1a1453fec6df15884
Source dataset
uspto-grants-2012_09
Patent number
US08263770B2

Reaction notes

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