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

HRID 485980Notes

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 chloroform-hexane 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 chloroform-hexane mixture

Sources & evidence

ORD record: ord-81b07f2ae90c49bd8a01d86d2b012271
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290478

Reaction notes

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