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Synlett

Volumn , Issue 20, 2007, Pages 3103-3106

An improved synthesis of amidoalkyl phenols involving a Ritter-type reaction

(4) Das, Biswanath a Laxminarayana, Keetha a Thirupathi, P a Ramarao, B a

a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY (India)

Author keywords

Amidoalkyl phenol; ortho quinone methide; Ritter reaction; Three component condensation

Indexed keywords

ALDEHYDE DERIVATIVE; NITRILE; PHENOL DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS;

EID: 37749037823 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990923 Document Type: Article

Times cited : (24)

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19
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- General Experimental Procedure: To a mixture of a phenol (1 mmol) and aromatic aldehyde (1 mmol) in MeCN or acrylonitrile (5 mL, triflic acid (10 mol, was added. The mixture was heated under reflux and the reaction was monitored by TLC After completion of the reaction, H2O (10 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL, The extract was dried and concentrated. The residue was subjected to column chromatography (silica gel; eluent: hexane-EtOAc, 4:1) to obtain the pure amidoalkyl phenol. The spectral (IR, 1H and 13C NMR and MS) data of some representative products are given below. Compound 4a: IR (KBr, 3422, 1654, 1511, 1460, 1376, 1269 cm-1. 1H NMR (200 MHz, CDCl3, DMSO-d6, δ, 8.99 (br s, 1 H, 8.01 (m, 1 H, 7.90 (br s, 1 H, 7.44-7.52 (m, 2 H, 6.84 (d, J, 8.0 Hz, 3 H, 6.68 (d, J, 8.0 Hz, 3 H, 1.92 (s, 3 H, 13C NMR 50 MHz
- +., 196 (33), 194 (100).

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