2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate, NMR, IR, MASS

LEARN SPECTROSCOPY THE PRACTICAL WAY WITH EXAMPLES






 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate (7) 

showed the following characterization data: mp 80–82 °C; R_f = 0.57 (hexane/EtOAc 9/1); 

¹H NMR (400 MHz, CDCl₃)
 δ: 2.76 (t, J = 7.9 Hz, 2 H), 2.97 (t, J = 8.3 Hz, 2H), 7.20 – 7.35 (m, 4 H), 7.40 (s, 2 H), 7.86 (s, 1H). 

The two -CH2- protons at dihydonapthalene ring appear at 2.76 and 2.97 as triplets


see¹H NMR pdf


¹³C NMR (100 MHz, CDCl₃) 
δ: 22.2, 27.4, 126.7, 126.9, 127.8, 128.5, 129.0, 129.8, 130.3, 131.8, 132.0, 137.2, 139.9, 143.3, 163.5.

The two -C- CARBONS on  dihydonapthalene ring appear at 22.2 and 27.2

^{see 13}C NMR pdf
 IR (ATR, neat)
 cm^-1: 1733 C=0, 1624, 1564, 1448, 1380, 1275, 1238, 1201, 1184, 1171, 1022, 958, 855, 757, 737, 714.

 HRMS (EI): m/z calcd for C₁₇H₁₂Cl₃O₂[M+H⁺] 352.9897, found 352.9896.


 Elemental Analysis: Anal. Calcd. for C₁₇H₁₁Cl₃O₂: C, 57.74; H, 3.14. Found: C, 57.72; H, 3.08.


CHECK OUT A ¹⁹F NMR BELOW FOR COMPD 2



 3,4-Dihydronaphthalen-2-yl trifluoromethanesulfonate (2) showed the following characterization data: R_f = 0.63 (hexane/EtOAc 9/1); 

¹H NMR pdf(400 MHz, CDCl₃) δ: 2.70 (t, J = 8.4 Hz, 2 H), 3.06 (t, J = 8.2 Hz, 2 H), 6.48 (s, 1 H), 7.05 – 7.10 (m, 1 H), 7.12 – 7.16 (m, 1 H), 7.17 – 7.23 (m, 2 H). 


¹³C NMR pdf(100 MHz, CDCl₃) δ: 26.5, 28.5, 118.5, 118.5 (q, ¹J_CF = 320.7 Hz), 127.3, 127.5, 128.4, 131.1, 132.9, 149.9. 


¹⁹F NMR pdf(376 MHz, CDCl₃) δ: –73.6.   ONE SIGNAL SEEN


IR (ATR, neat) cm^-1: 1664, 1416, 1248, 1202, 1137, 1062, 985, 895, 824, 753, 610. 


HMRS (EI): m/z calcd for C₁₁H₉F₃O₃S [M⁺] 278.0219, found 278.0222. 


Elemental Analysis: Anal. Calcd. for C₁₁H₉F₃O₃S: C, 47.48; H, 3.26. Found: C, 47.27; H, 3.19. 






2,4,6-Trichlorophenyl formate (6) showed the following characterization data: mp 72–73 °C; R_f = 0.57 (hexane/EtOAc 9/1); 

¹H NMR pdf(400 MHz, CDCl₃) δ: 7.41 (s, 2 H), 8.28 (s, 1 H).

 ¹³C NMR pdf(100 MHz, CDCl₃) δ: 128.7, 129.2, 132.6, 141.9, 156.2.


 IR (ATR, neat) cm^-1: 3078, 1732 C=O, 1563, 1447, 1385, 1227, 1085, 1057, 850, 820, 805, 678, 562. 

HRMS (ESI-TOF): m/z calcd for C₇H₃Cl₃O₂ [M⁺] 223.9194, found 223.9190. 


Elemental Analysis: Anal. Calcd. for C₇H₃Cl₃O₂: C, 37.29; H, 1.34. Found: C, 37.10; H, 1.40.