anisaldehyde

(redirected from 4-methoxybenzaldehyde)

anisaldehyde

[¦a·nəs′al·də‚hīd]
(organic chemistry)
C6H4(OCH3)CHO A compound with melting point 2.5°C, boiling point 249.5°C; insoluble in water, soluble in alcohol and ether; used in perfumery and flavoring, and as an intermediate in production of antihistamines.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
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A4 was synthesized by treating aniline 5mL (0.054mol) with 4-methoxybenzaldehyde 6.6ml (0.054mol) in toluene solvent by the stated method.
The Schiff bases were synthesized by condensation of 4-methoxybenzaldehyde with 2-chloroaniline, 3-chloroaniline, and 4-chloroaniline in the presence of ethyl alcohol as per the procedure described by Shah et al.
1-(4-(4,6-bis(phenylami-no)-1,3,5-triazin-2-ylamino)phenyl)-3-(4-methoxyphenyl)propen1one 177d was obtained from reaction of 176 with 4-methoxybenzaldehyde in good yield in DMF/KOH.
Entry Catalyst Catalyst Yield Time (mol %) (%) (min.) 5e Alum 3 66 110 5e ZnO nps 9 89 60 5e Mont K10 7 75 80 5e [P.sub.2][O.sub.5] 5 68 110 5e Acidic alumina 7 63 100 5e Silica 12 69 100 5e Mont KSF 7 58 90 5e Glacial acetic acid 12 60 90 Reaction conditions: hydrazine hydrate (1) (1 mmol), methyl acetoacetate (2) (1 mmol), 4-methoxybenzaldehyde (3) (1 mmol), and ethylcyano acetate (4) (1 mmol) in water (2 mL).
Table 3: Comparison of the yields with best methods found in the literatures Entry Aldehyde Isolated Literature best Yield (a) (%) yield (%)/Pyrrole: (%)/Pyrrole: aldehyde ratio aldehyde ratio 1 2-nitrobenzaldehyde 94/2:1 73/20:1 [11] 2 4-fluorobenzaldehyde 95/2:1 77/20:1 [11] 3 Benzaldehyde 97/2:1 86/03:1[13] 4 4-methoxybenzaldehyde 94/2:1 90/10:1 [14] 5 2,6-Dichlorobenzaldehyde 95/2:1 85/03:1[13] 6 4-methylbenzaldehyde 95/2:1 83/40:1 * [12] 7 4-chlorobenzaldehyde 97/2:1 77/20:1[11] 8 4-bromobenzaldehyde 92/2:1 74/40:1 * [12] (a) products were characterized by IR, [sup.1]H-NMR, MS (ES) and coincided with literature data, * pyrrole/imine ratio instead of pyrrole/aldehyde.
4-Amino-1,2,4- triazole 3 was converted to its Schiff bases 4a-c by refluxing with 4-chlorobenzaldehyde, 2-hydroxy1- naphthaldehyde and 4-methoxybenzaldehyde in acetic acid.
A solution of 3a,b (0.01 mol) in ethanol (30 mL) was treated with 0.01 mol of aromatic aldehydes such as 4-methoxybenzaldehyde and/or 4-chlorobenzaldehyde and few drops of TEA.