Reaction #1702066

Reaction equation

5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene

pivaloyl chloride

→

5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl tert-butyl ketone

Solvents

dichloromethane

Conditions

Workup

1. 1
   Washthe organic layer was washed by water
2. 2
   Dryinga saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   OtherThe crude product was purified by silica gel chromatography

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The TiCl4 in the reaction path stands for titanium chloride. To 5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene (409 mg, 2.00 mmol) were added titanium chloride (417 mg, 2.20 mmol) and pivaloyl chloride (361 mg, 2.99 mmol) followed by stirring at 120° C. for 1 hour. The reaction solution was diluted by dichloromethane, and the organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (40/3) as an elution solvent. The yield was 53.6 mg (9.0%).

Source