Synthesis of 2-benzylphenols: Transformation of the Baylis-Hillman adducts derived from 2-cyclohexen-1-one

Bulletin of the Korean Chemical Society

Volumn 24, Issue 4, 2003, Pages 409-410

  Lee, Ka Young ^a   Na, Jeong Eun ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

2 Benzylphenols; 2 Cyclohexen 1 one; Baylis Hillman adducts

Indexed keywords

2 CYCLOHEXENONE; BENZYL DERIVATIVE; PHENOL DERIVATIVE;

ACETYLATION; ARTICLE; BAYLIS HILLMAN REACTION; BIOTRANSFORMATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0037676133     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.4.409     Document Type: Article

References (21)

1. (a) Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209.
2. (b) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737.
3. Chung, Y. M.; Lee, H. J.; Hwang, S. S.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 799.
4. (a) Keum, G.; Lim, H. J.; Kang, S. B.; Kim, Y.; Chung, B. Y. Bull. Korean Chem. Soc. 2000, 21, 809.
5. (b) Yamato, T.; Fukumoto, M.; Sakaue, N.; Furusawa, T.; Tashiro, M. Synthesis 1991, 699.
6. (c) Teubner, H.; Kramer, A.; Weuffen, W.; Schrtter, E.; Grbel, G. EP 69,374 A2 (1983) (Chem. Abstr. 1983, 98, 215314q).
7. (d) Citterio, A.; Fancelli, D. EP 309,009 A1 (1989) (Chem. Abstr. 1989, 111, 133777r).
8. (e) Langer, R.; Buysch, H. J. EP 538,704 (1993) (Chem. Abstr. 1995, 122, 31111d).
9. (f) Yamaguchi, K.; Tanabe, Y.; Hasegawa, K.; Yamaguchi, A. EP 0,523,697 B1 (1993) (Chem. Abstr. 1993, 119, 149558).
10. Olah, G. A.; Olah, J. A.; Ohyama, T. J. Am. Chem. Soc. 1984, 106, 5284.
11. Goswami, A. J. Chem. Research (S) 2000, 554.
12. Regioselective synthesis of 2-benzylphenols from benzyl phenyl ether was achieved by using K10-montmorillonite, see Venkatachalapathy, C.; Pitchmamani, K.; Sivasultramanian, S. Indian J. Chem. 1998, 37B, 301. For the synthesis of 2-benzylphenol from the benzylation of the dianion of o-cresol, see Bates, R.; Siahaan, T. J. J. Org. Chem. 1986, 51, 1432.
13. Regioselective synthesis of 2-benzylphenols from benzyl phenyl ether was achieved by using K10-montmorillonite, see Venkatachalapathy, C.; Pitchmamani, K.; Sivasultramanian, S. Indian J. Chem. 1998, 37B, 301. For the synthesis of 2-benzylphenol from the benzylation of the dianion of o-cresol, see Bates, R.; Siahaan, T. J. J. Org. Chem. 1986, 51, 1432.
14. Gu, W.; Weiss, R. G. J. Org. Chem. 2001, 66, 1775.
15. Lau, C. K.; Williams, H. W. R.; Tardiff, S.; Dufresne, C.; Scheigetz, J.; Belanger, P. C. Can. J. Chem. 1989, 67, 1384.
16. Lee, K. Y.; Gong, J. H.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 659.
17. 3) δ 13.93, 22.44, 24.40, 27.25, 28.38, 31.52, 38.20, 123.99, 128.34, 131.79, 136.64, 199.49.
18. We examined the synthesis of 5a from 3a by direct dehydration. The reaction of 3a in benzene in the presence of p-TsOH showed the formation of complex mixtures. For the synthesis of similar 2-arylmethylphenols by direct dehydration in acidic medium in low yields, see (a) Patra, A.; Batra, S.; Joshi, B. S.; Roy, R.; Kundu, B.; Bhaduri, A. P. J. Org. Chem. 2002, 67, 5783. (b) Iwamura, T.; Fujita, M.; Kawakita, T.; Kinoshita, S.; Watanabe, S.-i.; Kataoka, T. Tetrahedron 2001, 57, 8455.
19. We examined the synthesis of 5a from 3a by direct dehydration. The reaction of 3a in benzene in the presence of p-TsOH showed the formation of complex mixtures. For the synthesis of similar 2-arylmethylphenols by direct dehydration in acidic medium in low yields, see (a) Patra, A.; Batra, S.; Joshi, B. S.; Roy, R.; Kundu, B.; Bhaduri, A. P. J. Org. Chem. 2002, 67, 5783. (b) Iwamura, T.; Fujita, M.; Kawakita, T.; Kinoshita, S.; Watanabe, S.-i.; Kataoka, T. Tetrahedron 2001, 57, 8455.
20. (a) Negishi, E.-i.; Owczarczyk, Z. R.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4453.
21. (b) Urdaneta, N.; Ruiz, J.; Zapata, A. J. J. Organometal. Chem. 1994, 464, C33.