Reaction #2314293

Reaction equation

alcohol

4-Methyl-3-cyclohexenol

p-toluenesulfonyl chloride

HCl

→

4-Methyl-3-cyclohexenol tosylate

Solvents

pyridine

Conditions

Workup

1. 1
   workup.WAITto stand at −20° C. for a further 16 hours
2. 2
   Extractionextracted with ethyl acetate
3. 3
   ExtractionThe combined organic layers are extracted with brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   OtherThe solvent is removed in vacuo

Procedure

To a solution of alcohol 4C (R=methyl) (10 g) and p-toluenesulfonyl chloride (20.8 g) in anhydrous tetrahydrofaran (21 mL) at 0° C. is added anhydrous pyridine (21 mL). The reaction is allowed to stir in an ice bath for 2 hours, and is then allowed to stand at −20° C. for a further 16 hours. The reaction mixture is then poured into 2M HCl (75 mL) and extracted with ethyl acetate. The combined organic layers are extracted with brine and dried over sodium sulfate. The solvent is removed in vacuo.

Source