5703-23-1

Basic information

• Product Name: 3-Hydroxy-4-methoxybenzeneacetaldehyde
• Synonyms: 3-Hydroxy-4-methoxybenzeneacetaldehyde;Homoisovanillin
• CAS NO: 5703-23-1
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 0
• Mol File: 5703-23-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Hydroxy-4-methoxybenzeneacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-methoxybenzeneacetaldehyde(5703-23-1)
• EPA Substance Registry System: 3-Hydroxy-4-methoxybenzeneacetaldehyde(5703-23-1)

Safety Data

• Hazardous Substances Data: 5703-23-1(Hazardous Substances Data)

Upstream product

• 34016-03-0 2-(3-benzyloxy-4-merhoxyphenyl)acetaldehyde 
• 84428-20-6 4-allyl-2-benzyloxy-1-methoxy-benzene 
• 50602-41-0 3-hydroxy-4-methoxyphenethyl alcohol 

Downstream Products

• 99168-52-2 (3-hydroxy-4-methoxy-phenyl)-acetaldehyde-semicarbazone 

Relevant articles and documents

Total Synthesis of the Ortho-Hydroxylated Protoberberines (S)-Govaniadine, (S)-Caseamine, and (S)-Clarkeanidine via a Solvent-Directed Pictet-Spengler Reaction

The common para regioselectivity in Pictet-Spengler reactions with dopamine derivatives is redirected to the ortho position by a simple change of solvents. In combination with a chiral auxiliary on nitrogen, this ortho-selective Pictet-Spengler produced the 1-benzyltetrahydroisoquinoline alkaloids (S)-crassifoline and (S)-norcrassifoline and the bioactive 1,2-dioxygenated tetrahydroprotoberberine alkaloids (S)-govaniadine, (S)-caseamine, and (S)-clarkeanidine with high enantiopurity. Ortho/para ratios up to 89:19 and diastereomeric ratios up to 85:15 were obtained during formation of the B-ring. The general applicability of this solvent-directed regioselectivity was demonstrated with a second Pictet-Spengler reaction as required for C-ring formation of caseamine (o/p = 14:86 in trifluoroethanol) and clarkeanidine (o/p = 86:14 in toluene).