Synthesis of Binaphthol-Derived Podands Based on Selective, Acid-Promoted Reaction of Benzylic Alcohols with Ethylene Glycols

Martin Hovorka; Ivan Stibor; Radim cigel; Ivana Smíková

doi:10.1055/s-1995-4926

Synlett 1995; 1995(3): 251-252
DOI: 10.1055/s-1995-4926

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Synthesis of Binaphthol-Derived Podands Based on Selective, Acid-Promoted Reaction of Benzylic Alcohols with Ethylene Glycols

Martin Hovorka^* , Ivan Stibor, Radim Šcigel, Ivana Smíšková

^*Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, The Czech Republic

Abstract

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3-Hydroxymethyl and 3,3’-bis(hydroxymethyl) binaphthols (1,2) react under acidic conditions smoothly with ethylene glycols to afford corresponding ethers 3 and 4, mostly in good to excellent yields. Screening experiments revealed that the reaction occurs efficiently with several different Lewis acids. Glycerine as glycol component gives a 7:1 mixture of 1^o-OH- and 2^o-OH-derived products 5 and 6. Monoalkyl derivatives of ethylene glycols are behaving in a similar way the reaction times being substantially longer.

6,6’,3,3’-substituted - 1,1’-binaphthalene-2,2’-diols - oligoethylene glycol monoethers - Lewis Acid promoted etherification

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