Benzyl Chloride → 4-(Benzyloxy)-3-hydroxybenzonitrile

HRID 2080126Notes

Reaction equation

HRID 2080126 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].CC(C)([O-])C.[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCCCCC>CS(C)=O.C(OCC)(=O)C>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 8058HexaneHCID 870653,4-DihydroxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 154534514-(Benzyloxy)-3-hydroxybenzonitrileYield 105.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-dihydroxy-benzonitrile (1.36 g, 10 mmol) and potassium tert-butoxide (1.5 g, 13 mmol) in dimethylsulfoxide (15 mL) was added benzyl chloride (1.5 mL, 13 mmol) under nitrogen atmosphere at room temperature, and the solution was stirred for 24 hours. Silica gel (100 mL) was added portionwise to the reaction solution for adsorption, a pale yellow oil of 4benzyloxy-3-hydroxy-benzonitrile (2.38 g) was obtained by silica gel column chromatography (hexane:ethyl acetate=7:3), in addition, this was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate, then ethyl acetate:methanol=90:10, then 85:15), and 4-benzyloxy-3-hydroxy-benzonitrile (0.588 g, 2.61 mmol, 24.8%) was obtained as a pale yellow solid.

Workup

  1. additionSilica gel (100 mL) was added portionwise to the reaction solution for adsorption

Sources & evidence

ORD record
ord-ced13054b4294deeac0e0e25bb668271
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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