Hydrochloric Acid → 1-cyano-2-naphthol

HRID 623245Notes

Reaction equation

HRID 623245 reaction equation
B(Cl)(Cl)Cl.[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:15].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+].Cl.CS[C:25]#[N:26]>ClCCCl>[C:25]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:15])#[N:26]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 86632-NaphtholHCID 11168Methyl thiocyanateHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 111164621-cyano-2-naphtholYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To 6 ml of a solution of 2.02M of boron trichloride in 1,2-dichloroethane were added a solution of 1.44 g of β-naphthol in 30 ml of 1,2-dichloroethane, 0.82 ml of methyl thiocyanate and 1.33 g of aluminium chloride under ice-cooling. After stirring at room temperature for 3 hr., the reaction mixture was poured into 33 ml of 4N aqueous NaOH and stirred at 75°-78° C. on an oil bath for 30 min. The reaction solution was mixed with 30 ml of 6N HCl and extracted with ether. After drying the ether layer over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized from ether-benzene to yield 1.49 g of 1-cyano-2-naphthol as crystals melting at 160°-161° C.

Workup

  1. temperaturecooling
  2. stirringstirred at 75°-78° C. on an oil bath for 30 min
  3. extractionextracted with ether
  4. dry with materialAfter drying the ether layer over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized from ether-benzene

Sources & evidence

ORD record
ord-37e668f76a2f4880951e11a7f80d83a2
Source dataset
uspto-grants-1988_09
Patent number
US04774331

Reaction notes

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