20736-21-4

Basic information

• Product Name: 1-(4-hydroxy-3-methoxyphenyl)-2-propanol
• Synonyms: 1-(4-hydroxy-3-methoxyphenyl)-2-propanol
• CAS NO: 20736-21-4
• Molecular Weight: 182.219
• Mol File: 20736-21-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(4-hydroxy-3-methoxyphenyl)-2-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-hydroxy-3-methoxyphenyl)-2-propanol(20736-21-4)
• EPA Substance Registry System: 1-(4-hydroxy-3-methoxyphenyl)-2-propanol(20736-21-4)

Safety Data

• Hazardous Substances Data: 20736-21-4(Hazardous Substances Data)

Upstream product

• 2503-46-0 1-(4-hydroxy-3-methoxyphenyl)2-propanone 
• 53940-49-1 2‐methoxy‐4‐(oxiran‐2‐ylmethyl)phenol 
• 7440-23-5 sodium 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 120-80-9 benzene-1,2-diol 

Relevant articles and documents

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A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans

A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.

Synthesis of Coniferyl and Dihydroconiferyl Derivatives Using Radical Bromination with N-Bromosuccinimide as the Key Step

Coniferyl and dihydroconiferyl derivatives have been synthesized by reacting bromides, obtained from allylic and benzylic brominations using N-bromosuccinimide (NBS), with appropriate nucleophiles.For instance, NBS bromination of eugenol acetate, followed by replacement of bromine by an acetoxy group and subsequent reduction with lithium aluminium hydride, afforded coniferyl alcohol in 65percent overall yield.Due to the availability of the starting materials (eugenol and isoeugenol) and the good overall yields obtained, these synthetic routes compete well with other methods of preparation.