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Optional ortho or alpha hydroxymethylation of alkylarenes

Treatment of arenes carrying Me or primary alkyl groups, e.g., EtPh, in THF with potassium tert-butoxide activated butyllithium followed by reaction with formaldehyde gives 2-arylalkanols, e.g., PhCHMeCH2OH. In contrast, if prior to the addn. of the electrophile a stoichiometric amt. of magnesium dibromide is added then the regioisomeric 2-alkylbenzyl alcs., e.g., 2-EtC6H4CH2OH, are formed. [on SciFinder (R)]

    Keywords: Regiochemistry (of hydroxymethylation of alkylarenes); Hydroxymethylation (regioselective ; of alkylarenes) ; regioselective hydroxymethylation alkylarene; alkanol aryl; benzyl alc alkyl

    Note:

    CAN 115:207587 25-7 Benzene, Its Derivatives, and Condensed Benzenoid Compounds Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0022-328X written in English. 50-00-0 (Formaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (hydroxymethylation by, of alkylarenes, regioselectivity in); 90-12-0 (1-Methylnaphthalene); 98-51-1; 100-41-4 (Ethylbenzene); 100-84-5 (1-Methoxy-3-methylbenzene); 108-88-3 (Toluene) Role: RCT (Reactant), RACT (Reactant or reagent) (hydroxymethylation of, regioselectivity in); 60-12-8P (Benzeneethanol); 89-95-2P; 767-90-8P; 773-99-9P (1-Naphthaleneethanol); 1123-85-9P; 5020-41-7P; 5406-86-0P; 52289-55-1P; 89244-39-3P; 96437-12-6P; 129716-13-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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