69471-28-9

Basic information

• Product Name: methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate
• Synonyms: methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate
• CAS NO: 69471-28-9
• Molecular Weight: 210.23
• Mol File: 69471-28-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate(69471-28-9)
• EPA Substance Registry System: methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate(69471-28-9)

Safety Data

• Hazardous Substances Data: 69471-28-9(Hazardous Substances Data)

Upstream product

• 93198-68-6 (E)-methyl 2’-hydroxy-4’-methoxycinnamate 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 144582-47-8 methyl 2'-acetoxy-4'-methoxycinnamate 
• 531-59-9 7-methoxycoumarin 
• 188782-91-4 3-[2-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-N-methyl-N-phenyl-propionamide 
• 188782-89-0 t-butyldimethylsilyl 3-(2'-t-butyldimethylsilyloxy-4'-methoxyphenyl)propanoate 
• 188782-90-3 3-[2-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionyl chloride 
• 21144-17-2 3-(2'-hydroxy-4'-methoxyphenyl)propanoic acid 
• 20921-02-2 7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one 
• 124-41-4 sodium methylate 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 

Downstream Products

• 108495-57-4 methyl 3-(4-methoxy-2-methoxycarbonylmethylthiophenyl)propionate 
• 16850-91-2 dehydrogeijerin 
• 117285-84-4 methyl 3-(5-benzoyl-2-hydroxy-4-methoxyphenyl)propanoate 
• 117285-76-4 methyl 3-(2-hydroxy-4-methoxy-5-senecioylphenyl)propanoate 
• 117285-83-3 methyl 3-(2-hydroxy-5-isobutanoyl-4-methoxyphenyl)propanoate 
• 117285-86-6 6-benzoyl-7-methoxycoumarin 
• 117285-75-3 methyl 3-(2-hydroxy-5-isovaleryl-4-methoxyphenyl)propanoate 
• 117285-82-2 methyl 3-(2-hydroxy-4-methoxy-5-propanoylphenyl)propanoate 
• 450-16-8 geijerin 
• 144582-50-3 methyl 3-(2-formyloxy-4-methoxyphenyl)propanoate 
• 117285-69-5 methyl 3-(2-isovaleryl-4-methoxyphenyl)propanoate 
• 117285-71-9 methyl 3-(4-methoxy-2-propanoyloxyphenyl)propanoate 
• 117285-74-2 methyl 3-(2-benzoyloxy-4-methoxyphenyl)propanoate 
• 117285-72-0 methyl 3-(2-isobutanoyloxy-4-methoxyphenyl)propanoate 

Relevant articles and documents

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

Conversion of 7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester

7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H- 1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable.

EFFICIENT, HIGHLY REGIOSELECTIVE FRIES REARRANGEMENTS OF METHYL 3-(2-ACYLOXY-4-METHOXYPHENYL)PROPANOATES: THE FIRST TOTAL SYNTHESIS OF THE LINEAR ACYLATED COUMARINS GEIJERIN AND DEHYDROGEIJERIN.

Aluminium chloride catalysed para-Fries rearrangement of methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (5) in nitromethane furnishes the corresponding 5-acylated products (6) cleanly and in high yield.The rearrangement products may be converted into 6-a