Water → (6-Hydroxy-2-naphthyl)-propanonitrile

HRID 372927Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:20])[C:18]#[N:19])[CH:11]=[CH:10]2.O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:20])[C:18]#[N:19])[CH:11]=[CH:10]2

Participants

Conditions

Temperature: -10 °C

Procedure

15.6 g of boron tribromide, were dissolved in 100 ml of methylene chloride and cooled to -10° C. To this, 80 ml of methylene chloride solution of 6.0 g oa (6-methoxy-2-naphthyl)-propanonitrile were added dropwise over 2 hours, followed by stirring for 7 hours at room temperature. The resulting reaction mixture was poured into 500 ml of iced water and extracted with ether, followed by washing the ether phase twice with water and then distilling off the solvent. The resulting solid was recrystallized with chloroformhexane mixture to obtain 4.5 g of oa (6-hydroxy-2-naphthyl)-propanonitrile.

Workup

customThe resulting reaction mixture
extractionextracted with ether
washby washing the ether phase twice with water
distillationdistilling off the solvent
customThe resulting solid was recrystallized with chloroformhexane mixture

Sources & evidence

ORD record: ord-e1f4f9665d2e4eceae50f68a07f5b52f
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05160662

Reaction notes

Loading…