ONE-POT SYNTHESIS OF SULFONEPHTHALEINS
1107
3,3-Bis(4-hydroxy-3-methylphenyl)-3H-2,1,k6-benzoxathiole-1,1-dioxide
(m-cresol purple) (Table 2, Entry 2). Mp: 296 ꢀC; IR (nujol): 2927.47, 2855.46,
1603, 1455.75, 1215.76, 757.18, 669.01 cmꢁ1
;
1H NMR (200 MHz, DMSO-d6 þ
CDCl3): d 1.05 (s, 6H), 6.10–6.13 (m, 2H), 6.75–6.81 (m, 4H), 6.93 (d, J ¼ 6 Hz,
1H), 7.00–7.10 (m, 2H), 7.35 (d, J ¼ 6 Hz, 1H); 13C NMR (300 MHz, DMSO-d6 þ
CDCl3): d 167.89, 154.79, 142.62, 138.68, 136.24, 133.83, 133.46, 127.82, 127.12,
119.85, 117.93, 77.43, 14.59; LCMS: 405.2 (Mþ þ Na), 383.3 (Mþ þ 1).
3,3-Bis(4-hydroxy-2,5-dimethylphenyl)-3H-2,1k6-benzoxathiole-1,1-
dioxide (p-xylenol blue) (Table 2, Entry 3). Mp: 215 ꢀC; IR (nujol): 3369.60,
2924.39, 2855.01, 1628.77, 1460.51, 1256.86, 761.76, 659.9 cmꢁ1
;
1H NMR
(200 MHz, DMSO-d6 þ CDCl3): d 1.45 (s, 12H), 5.91–6.03 (m, 2H), 6.45–6.68 (m,
3H), 6.76–6.88 (m, 2H), 7.50–7.61 (m, 1H); 13C NMR (200 MHz, DMSO-d6 þ
CDCl3): d 167.95, 154.37, 142.89, 138.37, 131.08, 128.03, 126.81, 126.35, 125.89,
77.46, 19.47, 13.70, LCMS (m=e): 411.2 (Mþ þ 1), 433.1 (Mþ þ Na).
3,3-Bis(2-amino-4-hydroxyphenyl)-3H-2,1k6-benzoxathiole-1,1-dioxide
(Table 2, Entry 4). IR (nujol): 3566.52, 3373.62, 3020.10, 1644.30, 1451.66, 1258.28,
753.14, 606.21 cmꢁ1; 1H NMR (200 MHz, DMSO-d6 þ CDCl3): d 6.85–6.92 (m, 6H),
6.99–7.02 (m, 2H), 7.03–7.05 (m, 2H); 13C NMR (200 MHz, DMSO-d6 þ CDCl3): d
167.72, 143.08, 137.56, 132.43, 130.56, 130.13, 126.91, 124.40, 121.75, 118.05, 77.0,
LCMS: 417.10 (Mþ þ 1). (Mp: not determined).
ACKNOWLEDGMENT
V. R. C. and D. K. D. are grateful to the National Academy of Sciences, India,
for the Senior Scientist Platinum Jubilee Fellowship and Project Assistantship,
respectively.
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