4-Hydroxybenzaldehyde → 3-[(4-Formylphenoxy)methyl]benzonitrile

HRID 130478

Reaction equation

HRID 130478 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:35]([C:34]1[CH:37]=[CH:38][C:31]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])=[CH:32][CH:33]=1)=[O:36]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 176086763-[(4-Formylphenoxy)methyl]benzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(Hydroxymethyl)benzonitrile (1.1 equiv), triphenylphosphine (1.1 equiv), and 4-Hydroxybenzaldehyde (1 equiv) in dry THF was added dropwise Diethyl azodicarboxilate (DEAD) (1.4 equiv). The reaction mixture stirred at room temperature overnight. The reaction was monitored by TLC. The solvent was removed under vacuum. It was purified by silica gel chromatography using Hexane:Ethyl acetate (3:1) to afford the title compound as a white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customIt was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b85e87cf6bf74ca8bdaa5cf2c0e17b8f
Source dataset
uspto-grants-2008_06
Patent number
US07381750B2

Linked notes

Loading…