13086-93-6

Basic information

• Product Name: (4-chlorophenyl)methanediyl diacetate
• Synonyms: (4-Chlorophenyl)methylene diacetate; (Acetyloxy)(4-chlorophenyl)methyl acetate; methanediol, 1-(4-chlorophenyl)-, diacetate; p-Chlorophenylmethanediol diacetate
• CAS NO: 13086-93-6
• Molecular Formula: C₁₁H₁₁ClO₄
• Molecular Weight: 242.6556
• Mol File: 13086-93-6.mol
• Article Data: 105

Chemical Properties

• Boiling Point: 321.2°C at 760 mmHg
• Flash Point: 129.8°C
• Density: 1.267g/cm³
• Vapor Pressure: 0.000302mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: (4-chlorophenyl)methanediyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-chlorophenyl)methanediyl diacetate(13086-93-6)
• EPA Substance Registry System: (4-chlorophenyl)methanediyl diacetate(13086-93-6)

Safety Data

• Hazardous Substances Data: 13086-93-6(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 6283-10-9 2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxane 
• 540-63-6 ethane-1,2-dithiol 
• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 106-43-4 para-chlorotoluene 
• 64-19-7 acetic acid 
• 116274-78-3 6-(4-Chloro-phenyl)-6,7-dihydro-5H-5,7,7a,13-tetraaza-benzo[3,4]cyclohepta[1,2-b]naphthalen-8-one 

Downstream Products

• 5333-82-4 2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol 
• 623-03-0 4-Cyanochlorobenzene 
• 132587-09-8 1-(4-chlorophenyl)-3-butenyl acetate 
• 77415-40-8 1-(4-Chlorophenyl)-1-propyl acetate 
• 104-88-1 4-chlorobenzaldehyde 
• 89978-12-1 2-chloro-2-(4-chlorophenyl)acetonitrile 
• 99074-23-4 cyano(4-chlorophenyl)methyl acetate 
• 5406-33-7 4-chlorobenzyl acetate 
• 1026157-80-1 1-(4-chlorophenyl)pentyl acetate 
• 958-06-5 (+/-)-(4-chlorophenyl)(phenyl)methyl acetate 
• 154866-92-9 ethyl 4-(4-chlorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxylate 
• 1008-94-2 5-(4-chloro-phenyl)-oxazole 
• 140-11-4 Benzyl acetate 
• 873-76-7 para-Chlorobenzyl alcohol 

Relevant articles and documents

NbCl5 as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions

A mild and efficient method for the chemoselective preparation of 1,1-diacetates catalyzed by NbCl5(5mmol%) under solvent-free conditions has been developed. The yields are in the range of 93-98%. This protocol offered several advantages, including low catalyst loading, good yields, short reaction times, and environmentally friendliness.

Solvent-free catalytic preparation of 1,1-diacetates using a silica-supported functional ionic liquid as catalyst

An efficient and convenient preparation of acylals from aldehydes and acetic anhydride, under solvent-free conditions, in the presence of a silica-supported functional ionic liquid, Si-[SbSipim][PF6], is reported. Si-[SbSipim][PF6] acts as a catalyst and can be recovered and reused four times without apparent loss of its catalytic activity.

1,3-Dibromo-5,5-dimethylhydantoin as catalyst for the conversion of aldehydes to their 1,1-diacetates (acetylals) under solvent-free and neutral conditions

Highly efficient and mild acetylation of aldehydes with acetic anhydride catalysed by 1,3-dibromo-5,5-dimethylhydantoin (DBH) was performed under neutral conditions to produce corresponding 1,1-diacetates (acetylals) in good to excellent yields.

A rapid preparation of acylals of aldehydes catalysed by Fe3+- montmorillonite

Aldehydes can be converted to acylals by treatment with acetic anhydride in the presence of Fe3+-montmorillonite in excellent yield at room temperature.

Synthesis of 1,1-Diacetates from Aldehydes using Trimethylchlorosilane and Sodium Iodide as Catalyst

A variety of aldehydes react with acetic anhydride in the presence of trimethylchlorosilane and sodium iodide or trimethylchlorosilane alone to afford 1,1-diacetates in excellent yields.

VSO4.5H2O: A mild and efficient catalyst for chemo-selective conversion of aldehydes to 1,1-diacetates

Protection of aliphatic and aromatic aldehydes as 1,1-diacetates using VSO4.5H2O under solvent-free conditions is carried out. The products are obtained in good to excellent yields. Ketones are not affected under these conditions.

A rapid, convenient and chemoselective synthesis of acylals from aldehydes catalyzed by reusable nano-ordered MCM-41-SO3H

Acylals were prepared by direct condensation of aldehydes with acetic anhydride using nano-ordered MCM-41-SO3H as a heterogeneous catalyst under solvent-free conditions at room temperature in a very short reaction time and excellent yields. The catalyst is recyclable, non-toxic, neither air nor moisture sensitive, and easy to handle. High chemoselectivity toward aldehydes in the presence of ketones is another advantage of the present method which provides selective protection of aldehydes in their mixtures with ketones.

Chemoselective synthesis of geminal diacetates (acylals) using eco-friendly reusable propylsulfonic acid based nanosilica (SBA-15-Ph-PrSO3H) under solvent-free conditions

An expeditious method for the acetylation of aldehydes by mesoporous solid sulfonic acid (SBA-15-Ph-PrSO3H) under solvent-free reaction conditions was described. The route furnished selectively and in excellent yields the corresponding 1,1-diacetates starting from aldehydes and acetic anhydride using the environmentally friendly catalyst. The catalyst was found to be highly active and selective and could be recycled several times.

An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2)

The synthesis of acylals from structurally diverse aldehydes has been performed in excellent yields under solvent-free conditions using HClO4-SiO2 as a mild, convenient, reusable, and heterogeneous catalyst. The procedure is operationally simple, environmentally benign and has the advantage of enhanced atom utilization. Furthermore, the catalyst can be recovered simply and reused efficiently a number of times without appreciable loss of activity.

Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O)

Aromatic and aliphatic aldehydes are transformed in 1,1-diacetates (acylals) in mild conditions, by a treatment with acetic anhydride and a Wells-Dawson acid (H6P2W18O62·24H 2O). gem-Diacetylation proceeds in Ac2O with a little as 1% mol Wells-Dawson acid at room temperature and under solventless conditions, obtaining very good to excellent yields (88-98%) of 1,1-diacetates (19 examples). Neither 4-dimethylaminobenzaldehyde nor ketones react under the same conditions.

PEG-supported sulfonic acid as an efficient and recyclable catalyst for the synthesis of 1,1-diacetates under solvent-free conditions

An operationally simple, efficient, and environmentally benign synthesis of 1,1-diacetates in good yields by reaction of different aldehydes with acetic anhydride in the presence of PEG-supported sulfonic acid under solvent-free conditions is described. C

Copper(II) tetrafluoroborate-catalyzed formation of aldehyde-1,1-diacetates

Aldehyde 1,1-diacetates are farmed in excellent yields from aldehydes and acetic anhydride under solvent-free conditions at room temperature in short times in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate.

An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes catalysed by expansive graphite

An easy preparation of 1,1-diacetates from aldehydes has been carried out in excellent yield under catalysis of expansive graphite at room temperature.

Amberlyst-15-catalyzed efficient synthesis of 1,1-diacetates from aldehydes

Amberlyst-15 was found to be an efficient catalyst for acylation reaction of aldehydes with acetic anhydride at room temperature in dichloromethane.

RuCl3·xH2O: A new efficient catalyst for facile preparation of 1,1-diacetates from aldehydes

An efficient, facile preparation of aldehyde 1,1-diacetates (acylals) in excellent yields catalyzed by RuCl3·xH2O is described. Ketones do not react under these conditions. Copyright Taylor & Francis Group, LLC.

PEG-SO3H as an efficient and reusable catalyst for chemoselective synthesis of 1,1-diacetates

An efficient and convenient procedure of the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature, in the presence of PEG-SO3H is reported. PEG-SO3H acts as a catalyst and can be recovered and reused eight times without apparent loss of its catalytic activity.

[HSO3-pmim][CH3SO3] as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under ultrasound irradiation

A mild and efficient method for the chemoselective preparation of 1,1-diacetates catalyzed by 1-methyl-3-(3- sulfopropyl)-imidazolium methyl sulfate under ultrasound irradiation has been developed. The yields are ranged in 90%-98%. This protocol offered several advantages including low catalyst loading, high yields, short reaction time and environmentally benign approach.

A simple and fast method for protection of aldehydes as 1,1-diacetates using cerium(IV) sulfate as an efficient and reusable inorganic catalyst

A simple, green, and very fast method for protection of aryl aldehydes as 1,1-diacetates promoted by cerium(IV) sulfate tetrahydrate, Ce(SO 4)2·4H2O, as a novel inorganic solid acid catalyst at room temperature and under solvent-free conditions is described. The present methodology offers several advantages, such as a simple procedure with an easy workup, very short reaction times, high yields, and the absence of any volatile and hazardous organic solvents. Copyright Taylor & Francis Group, LLC.

Highly efficient and chemoselective conversion of aldehydes to acylals catalyzed with tungsten hexachloride (WCL6)

Different types of aldehydes react chemoselectively with acetic anhydride in the presence of a catalytic amount of tungsten hexachloride (WCl6) to produce the corresponding gem-diacetates in good to excellent yields.

Iodine as Acetylation Catalyst in the Preparation of 1,1-Diacetates from Aldehydes

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Diacetates from aldehydes in the presence of zeolites

An easy preparation of diacetates from aldehydes and acetic anhydride in the presence of zeolites is reported.

Ultrasound-assisted synthesis of acylals from aldehydes using Mg(CH 3SO3)2-HOAC

An efficient method for the synthesis of acylals from different aldehydes and acetic anhydride in the presence of magnesium methanesulfonate-acetic acid under ultrasound irradiation at room temperature is achieved. Only 1.5mol% of magnesium methanesulfonate and a small quantity of acetic acid are needed to effect the reaction. Selective conversion of aldehydes is observed in the presence of ketones. The catalyst remains active and exhibits no substantial loss of activity or selectivity in up to three reaction cycles.

A facile and efficient conversion of aldehydes into 1,1-diacetates (acylals) using iron(III) fluoride as a novel catalyst

Aldehydes are smoothly converted into the corresponding 1,1-diacetates (acylals) in high yields in the presence of a catalytic amount (0.1 mol-%) of iron(III) fluoride at room temperature. The noteworthy features of the present system are shorter reaction times, chemoselective protection of aldehydes, and solvent-free conditions. The procedure is especially useful for large-scale syntheses as the catalyst is highly effective from the view of activity, selectivity, reusability, and economy in the preparation of 1,1-diacetates (acylals). CSIRO 2007.

Conjugate polymer-supported acid catalysts: An efficient and reusable catalyst for the synthesis of geminal diacetates (acylals) under solvent-free conditions

A comparative study on the catalytic activity of conducting polyaniline (PANI), polypyrrole (PPY), and poly-(3,4-ethylenedioxythiophene) (PEDOT) salts as solid acid catalysts for the synthesis of 1,1-diacetates (acylals) under solvent-free conditions has been presented. Use of the polypyrrole and poly-(3,4-ethylenedioxythiophene) salts as solid acid catalysts is reported for the first time. Preparation, recovery, and reusability of the catalysts were found to be good. Copyright Taylor & Francis Group, LLC.

Facile Synthesis of 1,1-Diacetates from Aldehydes Using Montmorillonite K-10 Clay under Microwave Irradiation

Selective and easy synthesis of acylals in dry media using montmorillonite K-10 clay in an Erlenmeyer flask under microwave activation in remarkably reduced reaction time is described.

Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes

The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.

Chemoselective synthesis of 1,1-diacetates under solvent-free condition using efficient heterogeneous ecofriendly catalyst: P2O5/kaolin

An efficient and chemoselective method for the preparation of acylals from different aldehydes and acetic anhydride using.....kaolin supported catalyst (P2O5). under solvent-free conditions is described herein. The present protocol offers several advantages including use of inexpensive and non-toxic catalyst support i.e., natural kaolin. Preparation of the supported catalyst is easy, the process is simple in operation, maintaining solvent free conditions, with short reaction times, high yields and affording selective protection of aldehyde in presence of ketone.