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10
Anodic Preparation
of 5
2,4-Dimethylphenol (1,
24.4 g, 0.2 mol) was mixed with 0.1 M Ba(OH)2˙8H2O
in MeOH (100 mL) and transferred into a nondivided standard electrolysis
cell equipped with two platinum sheets as anode and cathode, respectively.
At 25 ˚C a galvanostatic electrolysis with a current
density of 12.5 mA/cm² was performed.
During the electrolysis vigorous stirring is necessary and the formation
of 5 as a light brown precipitate can be
observed. After application of 33200 C (1.7 F/1) the precipitate was filtered off and
washed with MeOH (40 mL) to yield analytically pure 5 (12.7
g, 26.34 mmol, 52%) as colorless solid; mp 146-148 ˚C. ¹H
NMR (400 MHz, CDCl3): δ = 1.12
(s, 3 H), 1.53 (s, 3 H), 1.94 (d, J = 3
Hz, 3 H), 2.04 (s, 3 H), 2.20 (s, 3 H), 2.24 (s, 3 H), 2.29 (s,
3 H), 2.30 (s, 3 H), 5.05 (d, J = 2.16
Hz, 1 H), 5.17 (s, 1 H), 5.71 (s, 1 H), 6.08 (s, 1 H), 6.73 (d, J = 2.16 Hz,
1 H), 6.78 (s, 1 H), 6.85 (s, 1 H), 6.88 (dd, J = 8.19,
2.16 Hz, 1 H), 7.30 (d, J = 8.19
Hz, 1 H) ppm. ¹³C (100 MHz, CDCl3): δ = 15.03,
15.20, 15.34, 16.69, 20.63, 20.72, 20.85, 23.82, 46.80, 83.12, 84.66,
107.59, 119.63, 120.07, 120.28, 122.99, 123.67, 123.68, 126.89,
128.57, 128.96, 129.06, 130.47, 130.50, 131.28, 133.31, 133.74,
134.02, 134.43, 148.59, 156.74, 154.39 ppm. MS (EI, 70 eV): m/z (%) = 482.3
(34) [M]+
, 361.3
(100), 391.3 (33), 201.2 (76).
11 CCDC 686744 (5)
and CCDC 686745 (7), respectively, contain
the supplementary crystallographic data for this paper. These data
can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or
from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; fax: +44 (1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
