Dibutyltin oxide → 2-Hydroxy-4-octyloxy-benzonitrile

HRID 18456

Reaction equation

HRID 18456 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 2

HCID 61221Dibutyltin oxideHCID 104455702-Hydroxy-4-octyloxy-benzamide

Product 1

HCID 101060262-Hydroxy-4-octyloxy-benzonitrileYield 14.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-hydroxy-4-octyloxy-benzamide (5.21 g; 19.7 mmol) and dibutyltinoxide (3.65 g; 14.6 mmol) was refluxed in toluene (60 mL) for 12 days. The reaction mixture was evaporated to dryness on SiO2 and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:4) to yield 700 mg (14%) product as yellow crystals. Mp. 69-71° C. MS (Direct; Cl): 248 (MH+).

Workup

  1. customThe reaction mixture was evaporated to dryness on SiO2
  2. custompurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:4)

Sources & evidence

ORD record
ord-6c54fae39cb14701a9a8fe9b4c28e164
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Linked notes

Loading…