1-Naphthol → 1-Hydroxynaphthalene-2-carbonitrile

HRID 623246Notes

Reaction equation

HRID 623246 reaction equation
B(Cl)(Cl)Cl.[C:5]1([OH:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+].CS[C:24]#[N:25]>ClCCCl>[C:24]([C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[OH:15])#[N:25]

Participants

7

Reactant 5

HCID 70051-NaphtholHCID 11168Methyl thiocyanateHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125379991-Hydroxynaphthalene-2-carbonitrileYield 62%

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 α-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. After cooling the aqueous layer was washed with methylene chloride, acidified with 25 ml of 6N HCl and extracted with ether. After drying the ether layer over anhydrous magnesium sulfate, the solvent was distilled off. The residue (1.51 g) was purified on a column of 30 g of silica gel. Then 1.26 g of the eluate with 10% ethyl acetate-methylene chloride was recrystallized from ether-petroleum ether to give 1.04 g of 2-cyano-1-naphthol as crystals melting at 182°- 183° C.

Workup

  1. temperaturecooling
  2. stirringstirred at 75°-78° C. on an oil bath for 30 min
  3. temperatureAfter cooling the aqueous layer
  4. washwas washed with methylene chloride
  5. extractionextracted with ether
  6. dry with materialAfter drying the ether layer over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue (1.51 g) was purified on a column of 30 g of silica gel
  9. customThen 1.26 g of the eluate with 10% ethyl acetate-methylene chloride was recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-4866340278bb4d26ab5645638e4e43ec
Source dataset
uspto-grants-1988_09
Patent number
US04774331

Reaction notes

Loading…