7405-12-1

Usage

InChI:InChI=1/C8H10O2/c1-6-2-3-7(5-9)8(10)4-6/h2-4,9-10H,5H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 108-39-4 3-methyl-phenol 
• 59648-19-0 7-methyl-2-phenyl-4H-benzo[1,3,2]dioxaborinine 
• 110-88-3 1,3,5-Trioxan 
• 67-64-1 acetone 
• 4670-56-8 methyl 2-hydroxy-4-methylbenzoate 
• 698-27-1 4-methylsalicylaldehyde 

Downstream Products

• 64032-91-3 2,4-Bis-hydroxymethyl-5-methyl-phenol 
• 908001-79-6 2-acetoxymethyl-5-methylphenol 
• 908002-28-8 acetic acid 2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-benzyl ester 
• 857275-83-3 (2-hydroxy-4-methylphenyl)acetonitrile 
• 1174551-15-5 2-amino-3-benzoyl-6-methylbenzo[b]furan 

Relevant academic research and scientific papers

Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines

Efficient: A copper-catalyzed enantioselective intramolecular insertion of carbenoids into phenolic O-H bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBAr F=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright

The synthesis of 2-hydroxymethyl derivatives of phenols

2-Hydroxymethylphenols have been prepared in good yield by reduction with sodium borohydride of the precursor aldehydes, obtained regiospecifically from reaction of phenols with paraformaldehyde in toluene containing stannic chloride and tri-n-butylamine. By contrast, reaction of phenols with either paraformaldehyde under anhydrous conditions or with aqueous formaldehyde results in formation of both the hydroxymethyl and the bishydroxymethyl derivatives. Cyclic acetals of the precursor aldehydes are readily accessible.

Substituents on quinone methides strongly modulate formation and stability of their nucleophilic adducts

Electronic perturbation of quinone methides (QM) greatly influences their stability and in turn alters the kinetics and product profile of QM reaction with deoxynucleosides. Consistent with the electron-deficient nature of this reactive intermediate, electron-donating substituents are stabilizing and electron-withdrawing substituents are destabilizing. For example, a dC N3-QM adduct is made stable over the course of observation (7 days) by the presence of an electron-withdrawing ester group that inhibits QM regeneration. Conversely, a related adduct with an electron-donating methyl group is very labile and regenerates its QM with a half-life of approximately 5 h. The generality of these effects is demonstrated with a series of alternative quinone methide precursors (QMP) containing a variety of substituents attached at different positions with respect to the exocyclic methylene. The rates of nucleophilic addition to substituted QMs measured by laser flash photolysis similarly span 5 orders of magnitude with electron-rich species reacting most slowly and electron-deficient species reacting most quickly. The reversibility of QM reaction can now be predictably adjusted for any desired application.