7218-21-5

Basic information

• Product Name: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-2,6-dimethyl-
• CAS NO: 7218-21-5
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Mol File: 7218-21-5.mol

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-2,6-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-2,6-dimethyl-(7218-21-5)
• EPA Substance Registry System: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-2,6-dimethyl-(7218-21-5)

Safety Data

• Hazardous Substances Data: 7218-21-5(Hazardous Substances Data)

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 546-67-8 lead(IV) tetraacetate 
• 40430-74-8 Acetic acid (1R,2R,7S,8S,11S)-11-acetoxy-3,5,8,11-tetramethyl-4,12-dioxo-tricyclo[6.2.2.0^2,7]dodeca-5,9-dien-3-yl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 54350-32-2 2-(tert-butoxy)-1,3-dimethylbenzene 
• 61248-69-9 3-tert-Butyl-2,6-dimethyl-phenol 
• 61248-64-4 2-sec-Butoxy-1,3-dimethyl-benzene 
• 90460-53-0 (2RS,3Z,5E)-6-Acetoxy-2-methylhepta-3,5-diensaeure-N-cyclohexylamid 
• 576-26-1 2.6-dimethylphenol 
• 106675-94-9 3-Acetoxy-2,6-dimethylphenol 
• 709-17-1 4-Acetoxy-2,5-dimethylphenol 
• 880-06-8 4-hydroxy-3,5-dimethylphenyl acetate 
• 70024-45-2 3-Chlor-2,4-dimethyl-phenol 
• 13288-70-5 bis-(3,5-dimethyl-4-hydroxyphenyl)-sulfone 
• 20804-39-1 3-Acetoxy-2.4-dimethylbenzolsulfonylchlorid 
• 4674-18-4 S-(2,4-Dimethyl-3-hydroxy-phenyl)-mercaptoessigsaeure 
• 92190-72-2 (4-Hydroxy-3,5-dimethyl-phenyl)-phenyl-sulfon 
• 107775-28-0 3-Phenylsulfon-2,6-dimethyl-phenol 

Relevant articles and documents

Novel one-pot synthesis of acetoxy-2,4-cyclohexadienones

A new, simple, one-pot method for the oxidative acetylation of some substituted phenols leading to acetoxycyclohexa-2,4-dienones is described. A novel diacetoxycyclohexadienone 12 has also been prepared using the present method from 2-hydroxymethyl phenol (salicyl alcohol). Copyright Taylor & Francis, Inc.

Studies in the Synthesis of Polycyclopentanoids: Synthesis, Oxa-di-?-methane Rearrangement of Annulated Bicyclooctenones and Cyclopropane Ring Cleavage of Tetracyclo2,4.03,7>undecenones

A short, new and general approach for the synthesis of linear polyquinanes having the cis:anti:cis tricyclopentanoidal framework is delineated.The key element of this approach is the photochemical 1,2-acyl shift or oxa-di-?-methane rearrangement of annulated bicyclooctenones, having β,γ-unsaturated carbonyl chromophoric systems.An efficient method for the synthesis of a variety of annulated bicyclooctenones via inverse demand ?4s + ?2s cycloaddition of cyclohexa-2,4-dienones (9-12) with olefins (18-26) is reported.The structure of the adducts has been established through the study of their high-field 1H NMR and 13C NMR spectra and decoupling experiments.Synthesis of tricyclo2,6>undecadienones (51-57) from readily available adduct 43 has been achieved.Oxa-di-?-methane rearrangement of various chromophoric systems to polyquinanes (60-68) is described.The adduct 32 did not undergo oxa-di-?-methane rearrangement upon sensitized irradiation, while adduct 40 rearranged inefficiently to compound 64.Studies on the cleavage of the cyclopropane ring of the tetracyclic ketones (60, 66, 67 and 73) with formic acid and acetyl methanesulfonate is also reported.

?4s+?2s Cycloaddition: Synthesis, Structure and Oxa-di-? Rearrangement of Tricyclo2,6>undecadienones

A simple and efficient synthesis of tricyclo2,6>undecadienones (8-15) is described.The synthesis involves(i) Diels-Alder reaction of a cyclohexadienone (3) and various dienes (4-7) to furnish the keto-acetates (8-11) and (ii) base hydrolysis of 8-11 to the corresponding keto-alcohols (12-15).Photochemical oxa-di-? rearrangement of the cycloadducts (12,13, and 15) to linearly fused polyquinanes (16-18) is also described.The cycloadduct (14) fails to undergo rearrangement possibly due to quenching effect of dienic moiety in the annulated cyclopentene ring.

DIELS-ALDER CYCLOADDITION: SYNTHESIS AND OXA-DI-?-REARRANGEMENT OF TRICYCLO(5.2.2.02,6)UNDECADIENONE

A short synthesis of various tricyclo(5.2.2.02,6)undecadienones by Diels-Alder reaction of a 2,4-cyclohexadienone with dienes and their oxa-di-?-rearrangement is reported.

The stereochemistry and regiochemistry of Diels-Alder reactions of 6-acetoxy-2,6-dimethyl-2,4-cyclohexadienone

6-Acetoxy-2,6-dimethyl-2,4-cyclohexadienone (1) and maleic anhydride in boiling benzene give a single adduct, exo-5-acetoxy-1,5-dimethyl-6-oxobicyclooct-7-ene-endo-2,3-dicarboxylic acid anhydride (2).With propiolic acid 1 gives exo-5-hydroxy-1,5-dimethyl-6-oxobicycloocta-2,7-diene-2-carboxylic acid (15).The high stereoselectivity and regioselectivity of these reactions is interpretable in terms of orbital overlap, closed-shell repulsion, steric, and van der Waals-London effects.

Light-induced Reactions, XIV. Rules for Determining Spectra of 2,4-Cyclohexadien-1-ones

2,4-Cyclohexadien-1-ones of formula types 1 to 5 (cf.Fig. 1) provide basic values and positional increments for UV and 13C NMR spectra.These parameters allow to distinguish between constitutional isomers belonging to one and the same column of the graph of Fig. 1.It has become possible, e.g., to identify clearly the constitutional isomers 6 and 8 or 12 and 14, respectively.