I
D. Sang et al.
Paper
Synthesis
1H NMR (400 MHz, CDCl3): δ = 7.04 (d, J = 8.5 Hz, 2 H), 6.77 (d, J = 8.5
Hz, 2 H), 5.94 (ddt, J1 = 15.7 Hz, J2 = 10.6 Hz, J3 = 6.7 Hz, 1 H), 5.30 (s,
1 H), 5.04 (dt, J1 = 16.4 Hz, J2 = 1.6 Hz, 1 H), 5.03 (dt, J1 = 10.8 Hz,
J2 = 1.6 Hz, 1 H), 3.31 (dt, J1 = 6.6 Hz, J2 = 1.6 Hz, 2 H).
(13) Fache, F.; Suzan, N.; Piva, O. Tetrahedron 2005, 61, 5261.
(14) Kraft, P.; Eichenberger, W. Eur. J. Org. Chem. 2003, 3735.
(15) Zhao, H.; Brandt, G. E.; Galam, L.; Matts, R. L.; Blagg, B. S. Bioorg.
Med. Chem. Lett. 2011, 21, 2659.
(16) Coolen, H. K.; Meeuwis, J. A.; van Leeuwen, P. W.; Nolte, R. J.
J. Am. Chem. Soc. 1995, 117, 11906.
(17) Bhatt, M. V.; El-Morey, S. S. Synthesis 1982, 1048.
(18) Ozanne, A.; Pouységu, L.; Depernet, D.; Francois, B.; Quideau, S.
Org. Lett. 2003, 5, 2903.
(19) Pouységu, L.; Sylla, T.; Garnier, T.; Rojas, L. B.; Charris, J.;
Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 5908.
(20) Strych, S.; Trauner, D. Angew. Chem. Int. Ed. 2013, 52, 9509.
(21) Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. J. Agric. Food
Chem. 2008, 56, 8897.
13C NMR (100 MHz, CDCl3): δ = 153.64, 137.88, 132.38, 129.79,
115.57, 115.32, 39.38.
2-Phenethoxyphenol (8)
[CAS Reg. No. 33130-24-4]
A procedure for the preparation of alkyl aryl ethers was adopted.48
Phenethyl bromide (1.853 g, 10 mmol), catechol (7b; 1.103 g, 10
mmol), and K2CO3 (2.075 g, 15 mmol) were added to MeCN (40 mL),
and the mixture was stirred at 80 °C for 18 h before quenching with
aq 2 M HCl (20 mL). After extraction with EtOAc (3 × 50 mL), the or-
ganic phases were combined, washed with brine, and dried (anhyd
MgSO4). After filtration, the solvents were removed on a rotary evap-
orator, and the residue was purified by column chromatography (elu-
ent: PE/EtOAc 10:1) to afford the product as a colorless liquid; yield:
0.393 g (19%), which solidified after standing overnight at r.t.; mp 45–
46 °C (Lit.41 mp 48 °C); Rf = 0.54 (PE/EtOAc 10:1).
(22) Andersson, S. Synthesis 1985, 437.
(23) Tian, J.; Sang, D. ARKIVOC 2015, (vi), 446.
(24) Deffieux, D.; Gossart, P.; Quideau, S. Tetrahedron Lett. 2014, 55,
2455.
(25) Sang, D.; Yao, M.; Tian, J.; Chen, X.; Li, L.; Zhan, H.; You, L. Synlett
2017, 28, 138.
(26) Sang, D.; Wang, J.; Zheng, Y.; He, J.; Yuan, C.; An, Q.; Tian, J. Syn-
thesis 2017, 49, 2721.
(27) Tian, J.; Yi, C.; Fang, H.; Sang, D.; He, Z.; Wang, J.; Gan, Y.; An, Q.
Tetrahedron Lett. 2017, 58, 3522.
1H NMR (400 MHz, CDCl3): δ = 7.39–7.20 (m, 5 H), 6.92–6.81 (m, 4 H),
5.50 (s, 1 H), 4.26 (t, J = 6.8 Hz, 2 H), 3.12 (t, J = 6.8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 145.94, 145.63, 137.87, 128.89,
(28) Tian, J.; Yi, C.; He, Z.; Yao, M.; Sang, D. ChemistrySelect 2017, 2,
9211.
128.71, 126.76, 121.77, 120.12, 114.67, 112.16, 69.58, 35.78.
(29) Konwar, D.; Boruah, R. C.; Sandhu, J. S. Tetrahedron Lett. 1990,
31, 1063.
Funding Information
(30) Sarmah, P.; Barua, N. C. Tetrahedron Lett. 1988, 29, 5815.
(31) Babau, J. R.; Bhatt, M. V. Tetrahedron Lett. 1986, 27, 1073.
(32) Konwar, D.; Boruah, R. C.; Sandhu, J. S. Synthesis 1990, 337.
(33) Stauber, J. M.; Cummins, C. C. Inorg. Chem. 2017, 56, 3022.
(34) Tetsuo, A.; Takeshi, A.; Naomichi, F.; Shigeru, O. Bull. Chem. Soc.
Jpn. 1976, 49, 1441.
This work was supported by Jingchu University of Technology
(QDB201707) and Hubei Provincial Department of Education
(B2018234).
n
i
Jg
c
h
u
U
nveitrsi
y
of
Tech
n
o
lg
y
Q(
D
B
2
0
1
7
0
7
H)u
b
e
i
Porvniacil
D
e
p
artm
e
nt
of
E
d
u
coaitn
B(
2
0
1
8
2
3
4)
(35) Ren, H.; Chen, Z.; Cao, G.; Zhang, F.; Li, H.; Xu, J.; Miao, M. Synlett
2017, 28, 1795.
Supporting Information
(36) Bettanin, L.; Saba, S.; Galetto, F. Z.; Mike, G. A.; Rafique, J.; Braga,
A. L. Tetrahedron Lett. 2017, 58, 4713.
(37) Rafique, J.; Saba, S.; Rosario, A. R.; Braga, A. L. Chem. Eur. J. 2016,
22, 11854.
Supporting information for this article is available online at
S
u
p
p
ortioInfgrmoaitn
S
u
p
p
ortiInfogrmoaitn
(38) Saba, S.; Rafique, J.; Braga, A. L. Catal. Sci. Technol. 2016, 6, 3087.
(39) Shirshova, L. V.; Lavrent’ev, I. P. Russ. J. Coord. Chem. 2001, 27,
511.
(40) Ramanathan, S.; Sang, D.; Kumar, V.; Lemal, D. M. Synthesis of
Tetrafluorocatechol, In Efficient Preparations of Fluorine Com-
pounds; Roesky, H. W., Ed.; Wiley: Hoboken, 2012, 252.
(41) Klarmann, E.; Gates, L. W.; Shternov, V. A. J. Am. Chem. Soc.
1932, 54, 1204.
(42) Zuo, L.; Yao, S.; Wang, W.; Duan, W. Tetrahedron Lett. 2008, 49,
4054.
(43) Fields, D. L.; Miller, J. B.; Reynolds, D. D. J. Org. Chem. 1964, 29,
2640.
(44) Kuwatsuka, S.; Casida, J. E. J. Agric. Food Chem. 1965, 13, 528.
(45) Beekman, A. M.; Barrow, R. A. J. Org. Chem. 2014, 79, 1017.
(46) Hasse, K.; Willis, A. C.; Banwell, M. G. Eur. J. Org. Chem. 2011, 88.
(47) Fazary, A. E.; Ju, Y.-H.; Al-Shihri, A. S.; Bani-Fwaz, M. Z.; Alfaifi,
M. Y.; Alshehri, M. A.; Saleh, K. A.; Elbehairi, S. E. I.; Fawy, K. F.;
Abd-Rabboh, H. S. M. Open Chem. 2017, 15, 189.
(48) Sang, D.; Tian, J.; Ji, G. J. Fluoresc. 2006, 16, 749.
References
(1) Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249.
(2) Weissman, S. A.; Zewge, D. Tetrahedron 2005, 61, 7833.
(3) Ranu, B. C.; Bhar, S. Org. Prep. Proced. Int. 1996, 28, 371.
(4) Burwell, R. L. Jr. Chem. Rev. 1954, 54, 615.
(5) Zhou, P.; Hou, A.; Wang, Y. Chin. J. Org. Chem. 2018, 38, 156.
(6) Raju, G. G.; Raju, G. R.; Trimurtulu, G.; Venkateswarlu, S.; Kiran,
B. Patent WO2009 093259, 2009.
(7) Lange, R. G. J. Org. Chem. 1962, 27, 2037.
(8) Lange, R. G. US Patent 3256336, 1966.
(9) Yadav, Y.; Owens, E. A.; Sharma, V.; Aneja, R.; Henary, M. Eur.
J. Med. Chem. 2014, 75, 1.
(10) Shenoy, N. R.; Choughuley, A. S. J. Agric. Food Chem. 1989, 37,
721.
(11) Jeng, J. H.; Wang, Y. J.; Chang, W. H.; Wu, H. L.; Li, C. H.; Uang, B.
J.; Kang, J. J.; Lee, J. J.; Hahn, L. J.; Lin, B. R.; Chang, M. C. Cell. Mol.
Life Sci. 2004, 61, 83.
(12) Arifin, B.; Tang, D. F.; Achmadi, S. S. Indones. J. Chem. 2015, 15,
77.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–I