An Easy Two-Step Reduction of Salicylic Acids and Alcohols to 2-Methylphenols
18 July 2005 (online)
Salicylic acids and alcohols can be reduced to 2-methylphenols by a simple two steps procedure. Reaction conditions were optimized carrying out a study on the solvent effect and the amount of the reducing agent. The improved procedure resulted particularly useful in the synthesis of deuterated building blocks of biological interest.
reductions - deoxygenation - hydrides - phenols - hydrogenations
MazziniF. MandoliA. SalvadoriP. NetscherT. RosenauT. Eur. J. Org. Chem. 2004, 23: 4864
MazziniF. AlpiE. SalvadoriP. NetscherT. Eur. J. Org. Chem. 2003, 2003: 2840
MinamiN. KijimaS. Chem. Pharm. Bull. 1979, 27: 816
MitchellD. DoeckeCW. HayLA. KoenigTM. WirthDD. Tetrahedron Lett. 1995, 36: 5335
Seyden-PenneJ. Reductions by the Alumino- and Borohydrides in Organic Synthesis 2nd ed.: Wiley-VCH; New York: 1997.
BrownHC. KrishnamurthyS. Tetrahedron 1979, 35: 567
McLoughlinBJ. Chem. Commun. 1969, 540
MazziniF. NetscherT. SalvadoriP. J. Org. Chem. 2004, 69: 9303