Reaction #2329015

Reaction equation

2,3,-Dichloro-5,6-dicyano-1,4-benzoquinone

4-[2-(4-methoxy-benzyloxy)cyclohexyloxy]-2-trifluoromethyl-benzonitrile

methylene chloride

water

→

4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile

Yield 32.0%

Solvents

—

Hexanes

EA

EA

Conditions

Workup

1. 1
   OtherA solid formed
2. 2
   Filtrationwas filtered off
3. 3
   OtherThe resulting filtrate was passed through a silica plug and condensed under reduced pressure

Procedure

2,3,-Dichloro-5,6-dicyano-1,4-benzoquinone (hereinafter “DDQ) (18.2 g, 80.2 mmol) was added to a solution of 4-[2-(4-methoxy-benzyloxy)cyclohexyloxy]-2-trifluoromethyl-benzonitrile (17.77 g, 43.83 mmol), methylene chloride (500 mL) and water (50 mL). The reaction was allowed to stir at room temperature for 3 days. A solid formed and was filtered off. The resulting filtrate was passed through a silica plug and condensed under reduced pressure. A column was run using a gradient of 17-80% EA in Hexanes. A second column was run using 4:1 Hex:EA. This yielded the desired product, 4-(2-hydroxy-cyclohexyloxy)-2-trifluoromethyl-benzonitrile (4.0 g, 32% yield).

Source