99865-12-0

Basic information

• Product Name: 2-Buten-1-one, 1-(4-hydroxyphenyl)-3-methyl-
• CAS NO: 99865-12-0
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Mol File: 99865-12-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Buten-1-one, 1-(4-hydroxyphenyl)-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Buten-1-one, 1-(4-hydroxyphenyl)-3-methyl-(99865-12-0)
• EPA Substance Registry System: 2-Buten-1-one, 1-(4-hydroxyphenyl)-3-methyl-(99865-12-0)

Safety Data

• Hazardous Substances Data: 99865-12-0(Hazardous Substances Data)

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 108-95-2 phenol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 100-66-3 methoxybenzene 
• 54897-52-8 phenyl 3,3-dimethylacrylate 

Relevant articles and documents

A mild and convenient one-pot photochemical synthesis of chroman-4-one derivatives. the photo-Fries rearrangement of (hetero)aryl 3-methyl-2-butenoate esters under basic catalysis

The biphasic base catalysis-mediated photo-Fries rearrangement reaction of aryl 3-methy-2-butenoate esters in room temperature cyclohexane - 10% KOH system was investigated. This mild photochemical reaction leads to the formation of chroman-4-one derivatives in good to high yield and in short reaction times (30-120 min) in a one-pot photochemical reaction. Also, the photochemical reaction, as a convenient, versatile, and general method, applies efficiently to polycyclic and heterocyclic 3-methy-2-butenaote esters.

Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight

Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters in all the solvents studied and, depending on the proticity of the solvent, the latter involves an ESIPT process followed by thermal 6π-electrocyclic reaction and/or thermal (intramolecular oxa-Michael addition) cyclization of the ortho regioisomers photoformed. This second pathway is responsible of the formation of the 2,2-dimethylchroman-4-one derivatives.

On the synthesis of substituted 2,2-dimethyl1-4-chromanones and related compounds

A systematic study of the reaction of a series of monosubstituted phenols 3 and 3-methylbut-2-enoic acid 4 in phosphorus oxychloride/zinc chloride revealed that the formation of 4-chromanones was strongly infuenced by the substituents and their position on the aromatic ring of the starting phenols.