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Orcinol → 3-[2-(4-Cyanophenyl)ethoxy]-5-methylphenol

HRID 325049
Notes
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Reaction equation

HRID 325049 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([OH:27])[CH:26]=1.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38]O)=[CH:33][CH:32]=1)#[N:30].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][O:20][C:21]2[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([CH3:28])[CH:22]=2)=[CH:33][CH:32]=1)#[N:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10436OrcinolHCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 220335303-[2-(4-Cyanophenyl)ethoxy]-5-methylphenolYield 37%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Triphenylphoshine (7.86 g; 30 mmol), 3,5-dihydroxytoluene (2.5 g; 20 mmol) and 2-(4-cyanophenyl)ethanol (4.41 g; 30 mmol) were dissolved in THF (50 mL). Diethylazodicarboxylate (5.22 g; 30 mmol; dissolved in THF (10 mL)), was added and the solution was stirred at room temperature overnight. The solvent was removed in vacuo and the white solid residue extracted with Et2O. Purification by flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 1.85 g (37%) of the sub-title compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe white solid residue extracted with Et2O
  3. customPurification by flash chromatography (SiO2; toluene:EtOAc (10:1))

Sources & evidence

ORD record
ord-c75018db129c4a1882a1a70317255148
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06221898B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes