wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

0.295 g

635.10

0.0005

 

1.0

 

II

0.123 g

41.96

0.0029

 

6.0

 

III

5.0 mL

-

-

 

 

 

IV

2.5 mL

-

-

 

 

 

V

0.240 g

530.99

0.0005

 

 

(97%)

 

Procedure:  25 mL 1-neck flask, stirbar, septum, N2 inlet

                  Dissolved 0.295 g of diene I in 5.0 mL of absolute MeOH.  Stirred at rt.  Added 0.123 g of LiOH-H2O.  After 3 h TLC indicates product formation.  Added 2.5 mL of H2O and stirred for 1 h.  The reaction mixture was extracted with Et2O.  The organic layer was washed with 1 N NaOH, dried over MgSO4, filtered and the solvent was removed by rotary evaporation.  The product was a clear, colorless oil and was sufficiently pure at this stage.

 

notes

 

In this reaction, an alkaline hydrolysis is used to deprotect a benzoyl-protected hydroxyl group

In this reaction, an alkaline hydrolysis is used to deprotect a benzoyl-protected hydroxyl group.