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Abnormal base catalysed reaction of formaldehyde and benzaldehydes with 1-(2-hydroxyphenyl)-3-phenyl-1, 3-propanedione

✍ Scribed by S.J. Joglekar; S.D. Samant

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 188 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80065-9

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✦ Synopsis

1-(2-Apdroxyphenyll-3-phenyl-1,3-propanedione (la) reacts with formaldehyde in the presence of different 1-arylpiperasines (2) to form (1:l) inclusion compounds (3) which on column chromatographic separation yield 4,5,11,12-dibenzo-7-hydroxymethyl-l,3-dioxa-6,lO-dioxo-7,S-diphe~lcyclododecane (4) and the corresponding 2 1 react with formaldehyde in the presence of triethylamine to form 3-aroyl-3-(2,3-dihydro-4H-l-benzopyran-4-one-3-ylmethyl)-2,3-dihydro-4H-lbenzopyran-l-one (5) along with bencoic acids and with bentaldehydes in the presence of a base to give 2-aryl-2,3-dihydro-4H-1-bensopyran-4-one (61 9 10 Spectral data of 5 * IR (KRr, cm-l) = 1665 & 1690 (C=O). lE-NMR (CDCls) : 2 16-2.4 (m, lH, Coca); 2.67-3.0 (ID, 2H, -C-CRz-C); 3 98-4 4 (m, 2H, clcfti*~b* 1; 4.43 (d, lH, CC&flb, Jc*r=1282); 5 15 (d, 18, OciiaHb ,

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