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Cas Database

94611-94-6

94611-94-6

Identification

  • Product Name:3-methoxybenzoic acid anhydride

  • CAS Number: 94611-94-6

  • EINECS:

  • Molecular Weight:286.284

  • Molecular Formula: C16H14O5

  • HS Code:

  • Mol File:94611-94-6.mol

Synonyms:3-methoxybenzoic acid anhydride

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Relevant articles and documentsAll total 13 Articles be found

Metal-free cross-dehydrogenative coupling of aryl aldehydes to give symmetrical carboxylic anhydrides promoted by the TBHP/nBu4PBr system

Adib, Mehdi,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Mirzaei, Peiman,Jamal Addin Gohari, Seyed

, p. 3071 - 3074 (2016)

A novel, efficient, and metal-free dual C–O bond formation reaction for the synthesis of carboxylic anhydrides from aryl aldehydes via cross-dehydrogenative coupling is described. Heating a mixture of aromatic aldehydes and an aqueous solution of tert-butyl hydroperoxide as oxidant in the presence of catalytic nBu4PBr in chlorobenzene at 80?°C for 3?h afforded the corresponding carboxylic anhydrides in good to excellent yields.

Cu-MOF: An efficient heterogeneous catalyst for the synthesis of symmetric anhydrides: Via the C-H bond activation of aldehydes

Ahmadzadeh, Zahra,Mokhtari, Javad,Rouhani, Morteza

, p. 24203 - 24208 (2018/07/25)

In this paper, an efficient and straightforward synthetic approach for the preparation of a number of symmetric carboxylic anhydrides was reported using Cu2(BDC)2(DABCO) as an efficient heterogeneous catalyst via the C-H bond activation of aldehydes with excellent yields and simple work up. This C-H bond activation reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The Cu-MOF catalyst was recycled and reused four times without any loss of catalytic activity.

One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions

Liao, Yen-Sen,Liang, Chien-Fu

supporting information, p. 1871 - 1881 (2018/03/23)

In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.

An investigation on practical synthesis of carboxylic acid derivatives using p-toluenesulfonyl chloride

Eskandari, Parvin,Kazemi, Foad

, p. 431 - 439 (2017/07/24)

Carboxylic acid derivatives are well recognized as important class of reagents frequently used in the preparation of a variety of fine or special chemicals such as amides, esters, peptides, drugs, and dyes. Although several methods were developed for the preparation of these compounds, many of them present difficulties, including low yield, high reaction temperature, harsh reaction conditions, tedious work-up, and incompatibility with scale-up. Methods: The synthesis of carboxylic anhydrides is developed through the reaction of carboxylic acids with TsCl in the presence of K2CO3 and acetonitrile as a solvent under ultrasound irradiation and conventional conditions. In addition, one-pot synthesis of acyl azides was carried out in the presence of produced carboxylic anhydrides and the addition of sodium azide under identical condition. Results: A series of carboxylic anhydrides and acyl azides were synthesized using TsCl under ultrasound irradiation and conventional stirring with simple procedure, mild reaction conditions, high yields, and scale-up ability without any restriction. In most cases, the reaction under ultrasound irradiation was better in both yields and the reaction times compared to the conventional method. Conclusion: A convenient method has been developed for the preparation of carboxylic anhydrides and acyl azides under ultrasound irradiation and conventional stirring. The present method is practical and a highly effective alternative for previous reports. The major advantages of this method are: (i) simplicity of the procedure (ii) high yields and high purity of product (iii) scale-up capacity without considerable limitation in conventional system. Under ultrasound irradiation short reaction times as compared to conventional method are observed; yields are comparable to or better than conventional method.

Cu(I) catalyzed synthesis of anhydrides from aldehydes via CDC-pathway at ambient temperature

Nuree, Yasin,Singha, Raju,Ghosh, Munmun,Roy, Pronay,Ray, Jayanta K.

supporting information, p. 1479 - 1482 (2016/03/12)

A one-pot simple and concise methodology has been developed for synthesizing aromatic carboxylic anhydrides starting from easily accessible aromatic aldehydes using cuprous chloride as the catalyst and TBHP as the oxidant in DMSO solvent to garner moderate to good yields via radical pathway in short and convenient reaction time at room temperature.

Process route upstream and downstream products

Process route

carbon monoxide
201230-82-2

carbon monoxide

methoxybenzene
100-66-3

methoxybenzene

p-Anissaeure-anhydrid

p-Anissaeure-anhydrid

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

2-methoxybenzoic anhydride
64508-50-5

2-methoxybenzoic anhydride

p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

Conditions
Conditions Yield
With palladium diacetate; ethylene dibromide; at 100 ℃; for 20h; under 11400 Torr; Yield given. Further byproducts given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

methoxybenzene
100-66-3

methoxybenzene

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

2-methoxybenzoic anhydride
64508-50-5

2-methoxybenzoic anhydride

p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

C<sub>16</sub>H<sub>14</sub>O<sub>5</sub>

C16H14O5

Conditions
Conditions Yield
With palladium diacetate; ethylene dibromide; at 100 ℃; for 20h; under 11400 Torr; Yield given. Further byproducts given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

methoxybenzene
100-66-3

methoxybenzene

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

2-methoxybenzoic anhydride
64508-50-5

2-methoxybenzoic anhydride

p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

2,4'-dimethoxybenzoic anhydride

2,4'-dimethoxybenzoic anhydride

Conditions
Conditions Yield
With palladium diacetate; ethylene dibromide; at 100 ℃; for 20h; under 11400 Torr; Yield given. Further byproducts given. Yields of byproduct given;
3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

Conditions
Conditions Yield
With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
98%
With potassium carbonate; p-toluenesulfonyl chloride; In ethyl acetate; at 20 ℃; for 0.25h;
94%
With 2,6-dimethylpyridine; tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide; N,N-dimethyl-formamide; at 25 - 30 ℃; for 12h; Inert atmosphere; Photolysis;
92%
With potassium carbonate; p-toluenesulfonyl chloride; In acetonitrile; at 20 ℃; for 0.333333h;
92%
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate; In tetrahydrofuran; at 0 - 20 ℃;
73%
With phosphorus pentaoxide; toluene;
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

Conditions
Conditions Yield
With tert.-butylhydroperoxide; In acetonitrile; at 80 ℃; for 2h;
80%
With tert.-butylhydroperoxide; tetrabutyl phosphonium bromide; In chlorobenzene; at 80 ℃; for 3h; Sealed tube;
76%
With tert.-butylhydroperoxide; copper(l) chloride; In dimethyl sulfoxide; toluene; at 20 ℃; for 1h; Inert atmosphere;
75%
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In decane; acetonitrile; at 70 ℃; for 0.5h; Green chemistry;
24%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

Conditions
Conditions Yield
With 1,3-bis-(diphenylphosphino)propane; water; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 20 - 115 ℃; for 6h; under 760.051 Torr; Inert atmosphere; Autoclave;
95%
potassium 3-methoxybenzoate
74525-40-9

potassium 3-methoxybenzoate

m-anisoyl chloride
1711-05-3

m-anisoyl chloride

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

Conditions
Conditions Yield
With 1,4-diaza-bicyclo[2.2.2]octane; for 0.0833333h;
99%
With N-benzyl-N,N,N-triethylammonium chloride; In chloroform; at 20 ℃; for 2h;
98%
acetic anhydride
108-24-7

acetic anhydride

3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

Conditions
Conditions Yield
carbon monoxide
201230-82-2

carbon monoxide

methoxybenzene
100-66-3

methoxybenzene

p-Anissaeure-anhydrid

p-Anissaeure-anhydrid

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

2-methoxybenzoic anhydride
64508-50-5

2-methoxybenzoic anhydride

p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

Conditions
Conditions Yield
With palladium diacetate; ethylene dibromide; at 100 ℃; for 20h; under 11400 Torr; Yield given. Further byproducts given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

methoxybenzene
100-66-3

methoxybenzene

3-methoxybenzoic acid anhydride
94611-94-6

3-methoxybenzoic acid anhydride

2-methoxybenzoic anhydride
64508-50-5

2-methoxybenzoic anhydride

p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

C<sub>16</sub>H<sub>14</sub>O<sub>5</sub>

C16H14O5

Conditions
Conditions Yield
With palladium diacetate; ethylene dibromide; at 100 ℃; for 20h; under 11400 Torr; Yield given. Further byproducts given. Yields of byproduct given;

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