wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

4.50 mL

146.16

0.0016

1.099

1.0

 

II

7.055 g

69.49

0.1015

 

3.0

 

III

8.326 g

82.03

0.1015

 

3.0

 

IV

45 mL

-

-

 

 

 

V

18 mL

-

-

 

 

 

VI

4.680 g

161.20

0.0290

 

 

(86%)

 

Procedure:  250 mL 1-neck flask, stirbar, condenser, septum, N2 inlet

                  Dissolved 4.50 mL of tetralone I in 45 mL of MeOH.  Added 18 mL of water followed by 7.055 g of II and 8.326 g of NaOAc.  The reaction mixture was refluxed for 4.5 h and concentrated to half volume by rotary evaporation.  The mixture was diluted with 300 mL of water and the solid was collected by filtration.  The product was then recrystallized from straight hexanes.  The product was an off-white, flaky, crystalline solid. 

 

mp 99-100 C

 

1H NMR (CDCl3, 300 MHz) d 9.55 (s, OH, 1H), 7.90 (d, J = 8.0 Hz, ArH, 1H), 7.31-7.16 (m, ArH, 3H), 2.86 (t, J = 6.6 Hz, CH2, 2H), 2.78 (t, J = 6.3 Hz, CH2, 2H), 1.90 (m, CH2, 2H).