Phenol → 3-(3-Cyanophenyl)-5-(phenoxymethyl)benzoic acid methyl ester

HRID 1699737Notes

Reaction equation

HRID 1699737 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[CH:5]=1.[C:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH2:10][O:11][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9881809HCID 9881809, compound

Product 1

HCID 155499623-(3-Cyanophenyl)-5-(phenoxymethyl)benzoic acid methyl esterYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 mg of the 3-(3-cyanophenyl)-5-(hydroxymethyl)benzoic acid methyl ester produced in the production example 4 was dissolved in dry THF in the atmosphere of nitrogen, mixed with 10.5 mg of phenol, 35.4 mg of triphenylphosphine and 21 μl of azodicarboxylic acid diethyl ester at room temperature, and then stirred at room temperature overnight. The solvent was distilled away, and the residue was purified by silica gel chromatography to obtain 31 mg (77%) of the title compound (colorless, crystal).

Workup

  1. distillationThe solvent was distilled away
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3a218d2e5b0942f0a8ebff439558be5b
Source dataset
uspto-grants-2002_02
Patent number
US06348478B1

Reaction notes

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