3-Hydroxybenzyl alcohol → 3-(4-Formylphenoxy)benzonitrile

HRID 2266988Notes

Reaction equation

HRID 2266988 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.OC1C=C(C=CC=1)CO.[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24].C1C(C#N)=CN=C(Cl)C=1>>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 133943-CyanophenolHCID 680234-FluorobenzaldehydeHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 132385393-(4-Formylphenoxy)benzonitrile

Procedure

The title compound is prepared essentially as described in Preparation 1 substituting 4-fluorobenzaldehyde (0.85 mL, 8.06 mmol) for 3-hydroxybenzyl alcohol and 3-hydroxybenzonitrile (1.06 g, 8.86 mmol) for 6-chloronicotinitrile. Yield (0.90 g, 50%); 1H NMR (CDCl3) 10.01 (s, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.58-7.52 (m, 2H), 7.39-7.34 (m, 2H), 7.14 (d, J=8.5 Hz, 2H).

Workup

  1. customYield (0.90 g, 50%)

Sources & evidence

ORD record
ord-a0d9923fc3594cb38b1dd99d570e2c21
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

Loading…