Hydrochloric Acid → 6-Phenylnaphthalen-2-ol

HRID 2384516Notes

Reaction equation

HRID 2384516 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 124.5%

Reagents, catalysts & solvents 4

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

Procedure

In a three-necked flask were placed 17.9 g of 6-bromo-2-naphthol, 4.6 g of tetrakistriphenylphosphinepalladium and 200 ml of toluene and the mixture was stirred at room temperature. When the solids nearly dissolved, a solution of 9.8 g of phenylboronic acid in 200 ml of ethanol was added and stirred. Thereafter, a solution of 20 g of sodium carbonate in 200 ml of water was added and the mixture was stirred at room temperature 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 to give 22 g of 6-phenyl-2-naphthol. The amount of the unreacted 6-bromo-2-naphthol was 16%.

Workup

  1. customIn a three-necked flask were placed
  2. dissolutionWhen the solids nearly dissolved
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. additionwas added until the aqueous layer
  5. customthe organic layer was recovered
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3bc09c51fc2642e2ad1583ed3680056f
Source dataset
uspto-grants-2012_09
Patent number
US08263770B2

Reaction notes

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