ChemicalBook CAS DataBase List 3-hydroxy-5-Methylbenzonitrile

3-hydroxy-5-Methylbenzonitrile synthesis

6synthesis methods

Product Name:3-hydroxy-5-Methylbenzonitrile
CAS Number:95658-81-4
Molecular formula:C8H7NO
Molecular Weight:133.15

473923-98-7 Synthesis

473923-98-7
33 suppliers
inquiry

95658-81-4
57 suppliers
inquiry

Yield:95658-81-4 90%

Reaction Conditions:

with boron trichloride;tetra-(n-butyl)ammonium iodide in dichloromethane at -78 - 20;

Steps:

In a 100 mL round bottom flask, 3- methoxy-5-methyl-benzonitrile (500 mg, 3.39 mmol) was dissolved in 15 mL dry DCM, and tetrabutylammonium iodide (1.38 g, 3.73 mmol, 3.5 eq.) was added. The flask was cooled to -78 ⁰C. BCk (1 M in DCM, 11.87 mL, 33.16 mmol) was added to the reaction dropwise. The reaction mixture was stirred at -78 ⁰C and warmed up to room temperature overnight. The reaction mixture was quenched with ice and neutralized with saturated NaHCCh solution. DCM was added to extract the reaction mixture. The organic layer was concentrated down and purified (silica gel, 0-10% MeOH/DCM) to give a light yellow solid (408 g, 90%). LC-MS shows 132.0 (M-I). ¹H NMR (300 MHz, CDCb): δ 7.20 (s, 1 H), 6.96 (s, 1 H), 6.91 (s, 1 H), 2.37 (s, 3 H).

References:

WO2009/5674,2009,A2 Location in patent:Page/Page column 423; 424