Acrylic Acid Oxidation to Synthesize Methyl 3,3-dimethoxypropionate

Wang, Ke; Li, Wen Sheng; Zhou, Xiao Ping

doi:10.1007/s10562-005-8010-4

Cited by 2 publications

(1 citation statement)

References 8 publications

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“…Instead, an acetal derivative, methyl 3,3‐dimethoxypropanoate, was commercialized as a β‐aldo‐ester bifunctional building block. It can be prepared from acrylic acid and methanol through Wacker oxidation . Although some aliphatic aldo‐acid and ‐ester compounds have been used in the synthesis of heterocycles, compared with other AXB3 s, these compounds are less investigated.…”

Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Palladium-Catalyzed C–H Monoalkoxylation of α,β-Unsaturated Carbonyl Compounds

et al. 2016

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Contents1. General 2. Typical procedures to prepare the substrates 3. Typical procedure for the preparation of enol ether derivatives 4. Typical procedure for the introduction of amine substituent to the acrylic acid derivatives 5. Typical procedure for the introduction of phenyl substituent to the acrylic acid derivatives 6. References 7. NMR spectra of starting materials 8. NMR spectra of products GeneralThe 1 H NMR and 13 C NMR spectra were recorded by a JEOL JNM ECA-500 (500 MHz for 1 H NMR and 125 MHz for 13 C NMR), ECS-400 (400 MHz for 1 H NMR and 100 MHz for 13 C NMR), or AL-400 (400 MHz for 1 H NMR and 100 MHz for 13 C NMR) spectrometer. CDCl 3 , CD 2 Cl 2 or DMSO-d 6 was used as the solvent for the NMR measurements. The chemical shifts (δ) are expressed in part per million and internally referenced ( 1 H NMR: δ= 0.00; 13 C NMR; δ= 77.0 for CDCl 3 ; 1 H NMR: δ = 5.32;13 C NMR: δ = 53.3 for CD 2 Cl 2 ; 1 H NMR: δ = 2.49; 13 C NMR: δ = 39.5 for DMSO-d 6 ). The mass spectra (EI) were taken by a JEOL JMS Q1000GC Mk II Quad GC/MS. The IR spectra were recorded by a Brucker FT-IR ALPHA. The ESI high resolution mass spectra (HRMS) were measured by a Shimazu hybrid IT-TOF mass spectrometer. Typical procedures to prepare the substratesProcedure A: To a solution of acrylic acid (216 mg, 3.00 mmol) in DMF (5 mL) in a 50-mL round bottom flask equipped with a reflux condenser at 0 °C was added K 2 CO 3 (415 mg, 3.00 mmol). After 45 minutes, the alkyl chloride or alkyl bromide (2.50 mmol) was dropwise added, and the reaction mixture under an Ar atmosphere was stirred at 100 °C for 24 hours. The reaction mixture was cooled to room temperature, quenched with water (20 mL), and extracted with Et 2 O (20 mL × 2). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The residue was purified by silica-gel column chromatography using hexane-EtOAc or hexane-Et 2 O as the eluent to give the corresponding alkyl acrylate.Procedure B: To a solution of acrylic acid (288 mg, 4.00 mmol), N,N'-dicyclohexylcarbodiimide (DCC, 1.03 g, 5.00 mmol), and the phenol derivative (4.00 mmol) in CH 2 Cl 2 (20 mL) in a 50-mL round bottom flask was added N,N-dimethyl-4-aminopyridine (DMAP, 50.0 mg, 409 μmol) at room temperature. The mixture was sitirred under an Ar atmosphere for 24 hours, quenched with water (20 mL), and extracted with Et 2 O (20 mL × 2). The combined organic layers were dried over MgSO 4 , filtered, and concentrated in vacuo. The residue was purified by silica-gel column chromatography using hexane-EtOAc as the eluent to give the corresponding alkyl acrylate. 4-Nitrobenzyl Acrylate 1The reaction was carried out using 4-nitrobenzyl bromide (540 mg, 2.50 mmol) according to typical procedure A. 4-Nitrobenzyl acrylate was obtained in 82% yield (425 mg, 2.05 mmol) after purification by silica-gel column chromatography (Hexane/EtOAc = 10/1).

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Acrylic Acid Oxidation to Synthesize Methyl 3,3-dimethoxypropionate

Cited by 2 publications

References 8 publications

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Palladium-Catalyzed C–H Monoalkoxylation of α,β-Unsaturated Carbonyl Compounds

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