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Regioselectivity in the preparation of 2-hydroxy-4-methoxy benzaldehyde from resorcinol

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Relation http://ir.cftri.com/1221/
JMC_04_01
 
Title Regioselectivity in the preparation of 2-hydroxy-4-methoxy
benzaldehyde from resorcinol
 
Creator Pattekhan, H. H.
Divakar, S.
 
Subject 12 Aromatic Chemistry
 
Description Three reactions, namely, Reimer–Tiemann reaction of resorcinol, one pot Reimer–Tiemann reaction of resorcinol and its methylation and finally Reimer–Tiemann reaction of resorcinol monomethyl ether were studied. Better selectivities were observed in the first two reactions when b-cyclodextrin (b-CD) and its derivatives were employed. The formation of 2,4-dihydroxybenzaldehyde and 2-hydroxy-4-methoxybenzaldehyde from the first two reactions showed better conversion than the control reaction. In the process, 70.0% 2,4-dihydroxybenzaldehyde was detected in the presence of 1 equivalent of b-CD and 48.2% 2-hydroxy-4-methoxybenzaldehyde was detected in the presence of 0.2 equivalent of HPb-CD. However,Reimer–Tiemann reaction of resorcinol monomethyl ether resulted in only amarginal increase (43.9%) of 2-hydroxy-4-methoxybenzaldehyde
(I) in the presence of 0.2 equivalent of b-CD as compared to the control (35.2%). The observed results were explained in terms of specific orientation of resorcinol inside the b-CD cavity which facilitates the attack of
dichlorocbenzene from the narrower end on the electron rich ortho position to the –OH of resorcinol leading to the formation of 2,4-dihydroxybenzaldehyde or 2-hydroxy-4-methoxybenzaldehyde(I).
 
Date 2001
 
Type Article
PeerReviewed
 
Format application/pdf
 
Language en
 
Identifier http://ir.cftri.com/1221/1/Journal_of_Molecular_Catalysis_A_Chemical_169_%282001%29_185-191.pdf
Pattekhan, H. H. and Divakar, S. (2001) Regioselectivity in the preparation of 2-hydroxy-4-methoxy benzaldehyde from resorcinol. Journal of Molecular Catalysis A: Chemical, 160. pp. 185-191.