Organic reaction in water. Part 3: A facile method for reduction of aromatic rings using a Raney Ni-Al alloy in dilute aqueous alkaline solution under mild conditions

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5865-5868

  Tsukinoki, Takehito ^a   Kanda, Tadashige ^a   Liu, Guo Bin ^a   Tsuzuki, Hirohisa ^a   Tashiro, Masashi ^a  

^a TOHWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOY;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; REDUCTION;

EID: 0034729979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00636-5     Document Type: Article

References (26)

1. For Part 1 and Part 2, see: (a) Tsukinoki, T.; Mitoma, Y.; Nagashima, S.; Kawaji, T.; Hashimoto, I.; Tashiro, M. Tetrahedron Lett. 1998, 39, 8873-8876. (b) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991-5994.
2. For Part 1 and Part 2, see: (a) Tsukinoki, T.; Mitoma, Y.; Nagashima, S.; Kawaji, T.; Hashimoto, I.; Tashiro, M. Tetrahedron Lett. 1998, 39, 8873-8876. (b) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991-5994.
3. (a) House, H. O. Modern Synthetic Reactions; Benjamin: Menlo Park, 1972; pp. 1-227.
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17. Raney Ni-Al alloy (Ni: 50%) was purchased from the Kishida Chemical Company.
18. A typical procedure is described as follows: 1% aq. KOH solution (10 ml) was gradually dropped into a mixture of 1 (5 mmol, 650 mg), Raney Ni-Al alloy (3.5 g) and water (10 ml) for 1.5 h at 90°C under atmospheric pressure. After the reaction mixture was stirred for 4.5 h, the mixture was cooled to room temperature. The insoluble materials were filtered off with Celite and the residue was washed with ethyl acetate. The filtrate was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to afford 2 (639 mg, 94%) (Run 6).
19. When using a 5% aq. KOH solution under the same conditions as Run 4 in Table 1, the yield of 2 was 40%, but 1 was recovered (55%).
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22. When the reduction was undertaken by adding a Raney Ni-Al alloy over 1.5 h to a mixture of 10% aq. NaOH (10 ml) without any organic solvents and 1 (5 mmol) at 90°C, 1 was recovered (95%) (2: 2%). Furthermore, although the reaction was carried out by adding the Raney Ni-Al alloy at 60°C and then heating up the mixture to 90°C, the reaction did not proceed (1 was recovered quantitatively).
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25. (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
26. (b) Organic Synthesis in Water; Grieco, P., Ed.; Blackie Academic and Professional: London, 1998.