wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

35.0 mL

166.12

0.3418

1.134

1.0

 

II

61.856 g

-

-

 

 

 

III

500 mL

-

-

 

 

 

IV

33.984

130.15

0.2611

 

 

(76%)

 

Procedure:  1000 mL 1-neck flask, stirbar, cap

                  Dissolved 35.0 mL of levulinic acid (I) in 500 mL of absolute methanol.  Stirred at rt.  Added 61.856 g of IR-120 H+ resin.  After 48 h, the resin was removed by filtration through Celite and the solvent was removed by rotary evaporation.  The product was isolated by distillation (aspirator, 145 C) to afford the product as a clear colorless oil. 

 

1H NMR (CDCl3, 400 MHz) d 3.67 (s, CO2CH3), 2.75 (t, J = 6.5 Hz, H2), 2.57 (t, J = 6.5 Hz, H3), 2.19 (s, H5).