6335-18-8Relevant articles and documents
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Manske et al.
, p. 526,532 (1951)
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Competition of substituents for ortho direction of metalation of veratric acid
Chau, Nguyet Trang Thanh,Nguyen, Thi Huu,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
, p. 10552 - 10557 (2008/12/23)
LTMP (5 equiv) metalates randomly veratric acid (1). Under external quench conditions, the thermodynamically more stable lithium 2-lithio-3,4-dimethoxybenzoate (2) reacts with a variety of electrophiles to give versatile building units that are not easily accessible by conventional means. Under in situ quench conditions (LTMP/TMSCl), a reversal of regioselectivity is observed and 6-trimethylsilyl-3,4-dimethoxybenzoic acid (10) is formed predominantly.