Reaction #1121767

Reaction equation

imidazole

hydroquinone

tert-butyldimethylsilyl chloride

→

4-(tert-butyldimethylsilyloxy)phenol

Solvents

dimetylformamide

water

Conditions

Workup

1. 1
   Extractionwas extracted with 2×50 mL of ether
2. 2
   DryingThe combined organic layer was dried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated under reduced pressure
5. 5
   Otherpurified by column chromatography on silica gel with 5% ethyl acetate-hexanes

Procedure

A solution of 2.9 parts of imidazole, 1.99 parts of hydroquinone and 3 parts of tert-butyldimethylsilyl chloride in 10 mL of dimetylformamide was stirred at room temperature for 1 hr 45 min. The reaction was monitored by TLC showed formation of product. The reaction mixture was diluted with 50 mL of deionized water and product was extracted with 2×50 mL of ether. The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel with 5% ethyl acetate-hexanes to yield 2.24 parts 4-(tert-butyldimethylsilyloxy)phenol. NMR was used to confirm the following structure.

Source