5182-36-5

Basic information

• Product Name: FLOROPAL
• Synonyms: 2,4,6-Trimethyl-4-phenyl-1,3-dioxane;2,4,6-trimethyl-4-phenyl-3-dioxane;3-Dioxane,2,4,6-trimethyl-4-phenyl-1;FLOROPAL;Vertacetal;1,3-Dioxane, 2,4,6-trimethyl-4-phenyl-;2,4,6-Trimethyl-4-phenyl-1,3-dioxan;4-Phenyl-2,4,6-trimethyl-1,3-dioxane
• CAS NO: 5182-36-5
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28082
• EINECS: 225-963-6
• Mol File: 5182-36-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 278.7 °C at 760 mmHg
• Flash Point: 128.3 °C
• Appearance: /
• Density: 0.977 g/cm³
• Vapor Pressure: 0.00709mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: FLOROPAL(CAS DataBase Reference)
• NIST Chemistry Reference: FLOROPAL(5182-36-5)
• EPA Substance Registry System: FLOROPAL(5182-36-5)

Safety Data

• Hazardous Substances Data: 5182-36-5(Hazardous Substances Data)

Usage

Chemical Properties

It is a colorless to pale yellow liquid, d204 1.018–1.023, n20D 1.501–1.506, with a herbal, fresh odor, reminiscent of grapefruit. It is prepared by a Prins reaction of ??-methylstyrene with acetaldehyde and is used in perfume compositions for soap, detergents, and household products.

Preparation

The traditional product consists of a mixture of isomers containing about 60% of the sensorially more highly valued isomer. A product with a higher content of this isomer can be obtained by distillation . Correspondingly, this “Coeur” quality has a more strongly pronounced grapefruit note andmay therefore be used to impart fresh radiant grapefruit notes to modern personal care perfuming.

Trade name

Floropal (Symrise), Vertacetal? coeur (Symrise)

InChI:InChI=1/C13H18O2/c1-10-9-13(3,15-11(2)14-10)12-7-5-4-6-8-12/h4-8,10-11H,9H2,1-3H3

Upstream product

• 75-07-0 acetaldehyde 
• 98-83-9 isopropenylbenzene 
• 123-63-7 paracetaldehyde 

Downstream Products

• 77614-49-4 4-phenyl-pentan-2-ol 

Relevant articles and documents

Prins cyclization of styrenes or acetophenone catalyzed by DBSA in water

Dodecylbenzenesulfonic acid (DBSA) was proved to be an efficient catalyst for Prins cyclization of styrenes and formaldehyde or acetaldehyde in water. A tandem dehydration/ Prins cyclization reaction using a tertiary alcohol and formaldehyde as substrates proceeded very well by using DBSA as catalyst. Acetophenone, which is less reactive compared with styrene, can also react with formaldehyde when catalyzed by DBSA in water to afford 1,3-dioxan-5- ylphenylmethanone in good yield. Copyright Taylor & Francis Group, LLC.

Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel-Crafts acylation and Prins reaction in fluorous biphase system

In fluorous biphase system, hafnium(IV) bis(perfluorooctanesulfonyl)amide complex (Hf[N(SO2C8F17)2]4) was found to be a highly reactive and recyclable Lewis acid catalyst for Friedel-Crafts acylation and Prins reaction at significantly low catalyst loadings (≤1 mol%). In these reactions, Hf[N(SO2C8F17)2]4 is selectively soluble in the lower fluorous phase and can be recovered simply by phase separation. Furthermore, the catalyst can be reused without decrease of activity.

CONDENSATION D'ALCENES AROMATIQUES AVEC L'ACETALDEHYDE CATALYSEE PAR DES RESINES ECHANGEUSES D'IONS-II; STEREOISOMERISATION ET SYNTHESE DE NOUVEAUX DIOXA-1,3 CYCLOHEXANES POLYSUBSTITUES

The interconversion of the three stereoisomers of 4-anisyl-2,5,6 trimethyl-1,3 dioxacyclohexane, obtained from the condensation reaction between anethole and acetaldehyde, depends on the experimental conditions.In some cases, a reversal to the starting alkene could be observed: such a phenomenon does not seem to have been reported so far in the isomerization reactions of 1,3-dioxacyclohexanes.The data can be accounted for by a reaction mechanism involving various cationic intermediates.New 1,3-dioxacyclohexanes were obtained from acetaldehyde and various aromatic alkenes under mild reaction conditions in the presence of sulfonic ion-ex changers used as catalysts, in good yields and with high selectivity.