61235-37-8

Basic information

• Product Name: Benzaldehyde, 2-hydroxy-4-[(3-methyl-2-butenyl)oxy]-
• CAS NO: 61235-37-8
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 61235-37-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 2-hydroxy-4-[(3-methyl-2-butenyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2-hydroxy-4-[(3-methyl-2-butenyl)oxy]-(61235-37-8)
• EPA Substance Registry System: Benzaldehyde, 2-hydroxy-4-[(3-methyl-2-butenyl)oxy]-(61235-37-8)

Safety Data

• Hazardous Substances Data: 61235-37-8(Hazardous Substances Data)

Upstream product

• 62417-02-1 2,4-diprenyloxybenzaldehyde 
• 870-63-3 prenyl bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 

Downstream Products

• 1548331-50-5 (2E,5E)-2,5-bis{2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]benzylidene}cyclopentanone 
• 1448308-58-4 diethyl 3-[7-(3-methylbut-2-enyloxy)-2-oxo-2H-chromene-3-yl]-1-phenyl-1H-pyrazole-4,5-dicarboxylate 
• 1448308-36-8 7-[(3-methyl-2-butenyl)oxy]-3-{1-[(E)-2-phenylhydrazono]ethyl}-2H-chromen-2-one 
• 73569-44-5 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 
• 87080-25-9 2-Methoxy-4-acetoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 87080-26-0 4-Hydroxy-2-methoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 87080-24-8 2-Methoxy-4-(O-prenyl)-4'-methoxymethoxychalcone 
• 73569-46-7 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 
• 151410-32-1 (2E)-1-(4-hydroxyphenyl)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-en-1-one 
• 87080-27-1 licochalcone A 

Relevant articles and documents

Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: A facile approach for the synthesis of substituted 2H-chromene-3-carboxylates

A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a-v by the condensation of salicylaldehydes 1a-v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather than ester carbonyl due to a strong electron withdrawing effect and produced coumarin derivative 3a with the elimination of CHCl3.

Highly selective cleavage of prenyl ethers by means of a TiCl4-n-Bu4NI mixed reagent

Treatment of the prenyl ether of ethyl salicylate with a TiCl4-n-Bu4NI mixed reagent resulted in cleavage of the C-O bond to provide ethyl salicylate in quantitative yield. On the other hand, no cleavage reaction was observed when ethyl p-prenyloxybenzoate was used as a substrate. In this system, the cleavage reaction of ethers proved to be accelerated by the chelating effect of a neighboring group in the substrate.

Synthesis of Licochalcone-A

4,4'-Dihydroxy-2-methoxy-5-(α,α-dimethylallyl)chalcone (VII) (licochalcone-A) has been synthesised starting from β-resorcylaldehyde which on partial O-prenylation followed by methylation affords the aldehyde (II).The aldehyde (II) on condensation with p-methoxymethoxyacetophenone (III) under alkaline conditions affords the chalcone (IV), which on Claisen rearrangement yields the chalcone (V).Deacetylation and then demethoxymethylation of V by methanolic HCl affords licochalcone-A (VII), identical with a natural sample.