83088-21-5

Basic information

• Product Name: Benzaldehyde, 4-methoxy-3-[(2-methoxyethoxy)methoxy]-
• CAS NO: 83088-21-5
• Molecular Formula: C12H16O5
• Molecular Weight: 240.256
• Mol File: 83088-21-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 4-methoxy-3-[(2-methoxyethoxy)methoxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 4-methoxy-3-[(2-methoxyethoxy)methoxy]-(83088-21-5)
• EPA Substance Registry System: Benzaldehyde, 4-methoxy-3-[(2-methoxyethoxy)methoxy]-(83088-21-5)

Safety Data

• Hazardous Substances Data: 83088-21-5(Hazardous Substances Data)

Upstream product

• 621-59-0 isovanillin 
• 3970-21-6 2-Methoxyethoxymethyl chloride 

Downstream Products

• 117048-62-1 combrestatin A₄ 
• 1362101-22-1 (4-methoxy-3-(2-methoxyethoxymethoxy)phenyl)(3,4,5-trimethoxyphenyl)methanone 
• 1362101-30-1 (Z)-5-(3-((2-methoxyethoxy)methoxy)-4-methoxystyryl)-1,2,3-trimethoxybenzene 
• 1362101-28-7 5-(2-(3-((2-methoxyethoxy)methoxy)-4-methoxyphenyl)ethynyl)-1,2,3-trimethoxybenzene 
• 1362101-26-5 (+/-)-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-(1H-tetrazol-5-yl)(3,4,5-trimethoxyphenyl)methanol 
• 1362101-24-3 (+/-)-(1-allyl-1H-tetrazol-5-yl)(4-methoxy-3-(2-methoxyethoxymethoxy)phenyl)(3,4,5-trimethoxyphenyl)methanol 
• 1362101-20-9 (+/-)-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-(3,4,5-trimethoxyphenyl)methanol 
• 1161395-25-0 (Z)-3-(3-methoxyethoxymethyl-4-methoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 71135-74-5 5-(3,5-dimethoxyphenylethyl)-3,4-dihydroxy-8-methoxy-2,2-dimethyl-2H-chromen 

Relevant articles and documents

Dehydrative fragmentation of 5-hydroxyalkyl-1 h -tetrazoles: A mild route to alkylidenecarbenes

The development of a mild, base-free method for the generation of alkylidenecarbenes is reported. Treatment of 5-hydroxyalkyl-1H-tetrazoles with carbodiimides generates products arising from the 1,2-rearrangement or [1,5]-C-H bond insertion of a putative alkylidenecarbene. Formation of this divalent intermediate is proposed to occur by way of a tetraazafulvene, which undergoes extrusion of 2 mol of dinitrogen. Details of this methodology, its application to the synthesis of combretastatin A-4, and an improved route to 5-hydroxyalkyl-1H-tetrazoles are described.

Dihydrostilbenes of Cannabis. Synthesis of Canniprene

Canniprene (10) is synthesised via reaction of a phenolate-anion ylide with a benzyl-protected aldehyde.Benzoylation, followed by hydrogenation and hydrogenolysis of the resulting stilbene, leads to a half-benzoylated bibenzyl which is converted into its O-dimethylprop-2-ynyl derivative.Semi-hydrogenation, Claisen rearrangement, and debenzoylation gives canniprene.In a second synthesis the prenylated (3-methylbut-2-enylated) and benzyl-protected ring-B section is made first and converted by Wittig reaction into a dibenzyl-protected stilbene.The stilbene is reduced and the benzyl groups removed in one step, without affecting the prenyl group, by sodium in butanol: magnesium in methanol is capable of stilbene reduction without debenzylation.This practical synthesis proceeds in 19 percent overall yield from the dimethylprop-2-ynyl ether of isovanillin (14) and is applicable to isotopelabelling.The use of p-bromophenacyl (PBP) ether and methoxyethoxymethyl (MEM) ether protection as the basis for canniprene synthesis is also considered.Other bibenzyls relevant to the natural products of Cannabis are made and the methylated chroman (37) derived from canniprene is also synthesised.