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Tuesday 29 January 2019

Photo-organocatalytic synthesis of acetals from aldehydes

Graphical abstract: Photo-organocatalytic synthesis of acetals from aldehydes

Abstract

A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied

Photo-organocatalytic synthesis of acetals from aldehydes

 
 Author affiliations
https://pubs.rsc.org/en/Content/ArticleLanding/2019/GC/C8GC03605E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract
STR1
(3,3-Dimethoxypropyl)benzene (2a)6
Colorless oil; 95% yield; 1H NMR (200 MHz, CDCl3) δ: 7.33-7.18 (5H, m, ArH), 4.37 (1H, t, J = 5.8 Hz, OCH), 3.33 (6H, s, 2 x OCH3), 2.68 (2H, t, J = 7.6 Hz, CH2), 1.98- 1.87 (2H, m, CH2); 13C NMR (50 MHz, CDCl3) δ: 141.8, 128.4, 125.9, 103.7, 52.8, 34.0, 30.8; MS (ESI) m/z 181 [M+H]+ .
6. Q. Zhou, T. Jia. X.-X. Li, L. Zhou, C.-J. Li, Y. S. Feng, Synth. Commun., 2018, 48, 1068.
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Friday 20 October 2017

2,3-dihydrobenzofuran

2,3-Dihydrobenzofuran 99%

2,3-Dihydrobenzofuran

  • CAS Number 496-16-2
      
  •  
  • Empirical Formula (Hill Notation) C8H8O
      
  •  
  • Molecular Weight 120.15
  •  Beilstein Registry Number 111928
      




http://www.rsc.org/suppdata/gc/c4/c4gc01822b/c4gc01822b1.pdfhttp://www.rsc.org/suppdata/gc/c4/c4gc01822b/c4gc01822b1.pdf


1H NMR




MASS
Image result for nmr 2,3-dihydrobenzofuran
IR



UV




1H NMRPREDICT


13C NMR PREDICT




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Monday 9 October 2017

A green route for methanol carbonylation


Catal. Sci. Technol., 2017, Advance Article
DOI: 10.1039/C7CY01621B, Paper
Youming Ni, Lei Shi, Hongchao Liu, Wenna Zhang, Yong Liu, Wenliang Zhu, Zhongmin Liu
Halide-free and noble metal-free pyridine-modified H-mordenites exhibit high stability and selectivity in methanol carbonylation to acetic acid.

A green route for methanol carbonylation

 Author affiliations

Abstract

Acetic acid is one of the most important bulk commodity chemicals and is currently manufactured by methanol carbonylation reactions with rhodium or iridium organometallic complexes and halide-containing promoters named Monsanto or BP Cativa™ homogeneous processes, respectively. Developing a halide-free catalyst and a heterogeneous process for methanol carbonylation is of great importance and has recently attracted extensive research attention. Here, we report a green route for direct synthesis of acetic acid via vapor-phase carbonylation of methanol with a stable, selective, halide-free, and noble metal-free catalyst based on pyridine-modified H-mordenite zeolite. Methanol conversion and acetic acid selectivity can reach up to 100% and 95%, respectively. Only little deactivation is observed during the 145 hour reaction.
 
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Sunday 17 September 2017

Endo-4,7-bis(hydroxymethyl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (endo-4,7- bis(hydroxymethyl)norcantharimide)






Endo-4,7-bis(hydroxymethyl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (endo-4,7- bis(hydroxymethyl)norcantharimide), 4 (method A)

Endo-4,7-bis(hydroxymethyl)norcantharimid-5-ene (120 mg, 0.53 mmol) was dissolved in water (3 mL), Pd/C 10% was added (15 mg) and reaction mixture was placed under hydrogen atmosphere for 8 h at 24 °C. Catalyst was filtered off and washed thoroughly with water (3 × 3 mL), filtrate was evaporated under reduced pressure. Target compound 4 was obtained as white solid, yield 87% (110 mg).

1H NMR (D2O) = 3.76 (s, 4H), 3.46 (s, 2H), 1.61-1.72 (m, 4H);

1H NMR (DMSO-d6) = 11.10 (s, 1H), 5.08 (s, 2H), 3.66 (s, 4H), 3.37 (s, 2H), 1.71 (m, 2H), 1.49 (m, 2H);

13C NMR (D2O) = 179.0, 88.8, 60.7, 52.3, 27.0 ppm.

m/z HRMS (ESI) Calcd. for C10H13NO5 [M+Na]: 250.0686. Found 250.0696.

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC02211E, Paper
F. A. Kucherov, K. I. Galkin, E. G. Gordeev, V. P. Ananikov
Efficient one-pot synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described using a [4 + 2] cycloaddition reaction.

Efficient route for the construction of polycyclic systems from bioderived HMF

 Author affiliations
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Friday 19 May 2017

Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00657H, Paper
Nelly Ntumba Tshibalonza, Jean-Christophe M. Monbaliu
Highly selective flash deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions.

Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions



Image result for Nelly Ntumba Tshibalonza



Ms. Nelly Tshibalonza Ntumba

Nelly Tshibalonza
Nelly Tshibalonza was born in 1983 in Kinshasa, Congo. She received her diploma degree in Chemistry in 2006 from the University of Kinshasa. She is currently a fellow of the Belgian Technical Cooperation and is preparing a Ph.D. thesis on the development of catalytic methods to enhance the value of renewable raw materials.
E-mail: nel.tshibalonza@student.ulg.ac.be
Telephone: +32 (0)4 366-3493




http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC00657H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract


Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

 Author affiliations

Abstract

The deoxydehydration (DODH) of glycerol towards allyl alcohol was revisited under continuous-flow conditions combining a microfluidic reactor setup and a unique reactive dynamic feed solution approach. Short reaction times, high yield and excellent selectivity were achieved at high temperature and moderate pressure in the presence of formic acid, triethyl orthoformate, or a combination of both. Triethyl orthoformate appeared as a superior reagent for the DODH of glycerol, with shorter reaction times, lower reaction temperatures and more robust conditions. In-line IR spectroscopy and computations provided different perspectives on the unique reactivity of glycerol O,O,O-orthoesters.
Graphical abstract: Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

Image result for Jean-Christophe M. Monbaliu

photo_JC_Monbaliu
JC M. Monbaliu, PhD.
Lecturer
Department of Chemistryjc.monbaliu@ulg.ac.be
t +32 (0) 4 366 35 10

Jean-Christophe M. Monbaliu

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Saturday 25 February 2017

2-Methoxy-4-propylphenol

 
2-Methoxy-4-propylphenol
2-Methoxy-4-propylphenol
1H NMR (400 Mhz, CDCl3) δ (ppm): 6.83 (1H,d, J = 7.8 Hz), 6.68 (2H, d, J = 7.4 Hz), 5.47 (1H, s), 3.79 (3H, s), 2.52 (2H, t, J =7.6 Hz), 1.61 (2H, sext, J = 7.5 Hz) 0.94 (3H, t, J = 7.3 Hz).
13C NMR (100 MHz, CDCl3) δ (ppm) 146.4, 143.6,134.7, 121.0, 114.2, 111.1, 55.9, 37.8, 24.9, 13.8.
HRMS (ESI-TOF) m/z: [M + H]+ calculated for C10H15O2:167.1067; found: 167.1064.
DOI: 10.1021/acs.oprd.6b00441
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Saturday 21 January 2017

Metal-free radical C-H methylation of pyrimidinones and pyridinones with dicumyl peroxide






Metal-free radical C-H methylation of pyrimidinones and pyridinones with dicumyl peroxide


Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03355E, Communication
Pei-Zhi Zhang, Jian-An Li, Ling Zhang, Adedamola Shoberu, Jian-Ping Zou, Wei Zhang
A method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely. The product was separated by crystallization and the byproducts were recovery by distillation

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03355E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide

Pei-Zhi Zhang,a   Jian-An Li,a   Ling Zhang,a  Adedamola Shoberu,a   Jian-Ping Zou*a and  Wei Zhang*b  
*
Corresponding authors
a
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, China
 E-mail: jpzou@suda.edu.cn
b
Centre for Green Chemistry and Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, USA
 E-mail: wei2.zhang@umb.edu
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03355E


























A new method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide (DCP) under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely at the desired concentration. The reaction solvent and DCP derivative were readily recovered by distillation. The product was purified by crystallization to minimize the amount of waste.


2,6-diphenyl-5-methylpyrimidinone







Colorless solid, mp 258−260 °C, 73% yield (191 mg).

1H NMR (400 MHz, DMSO-d6): δ 12.85 (s, 1H), 8.17 (d, J = 7.1 Hz, 2H), 7.68 (d, J = 6.6 Hz, 2H), 7.53 (dd, J = 14.3, 6.8 Hz, 6H), 2.10 (s, 3H).

13C NMR (101 MHz, CDCl3): δ 161.15, 152.97, 138.68, 132.26, 131.62, 129.11, 129.02, 128.86, 128.15, 127.45, 119.09, 12.65.

 HRMS (ESI-TOF) m/z: (M+H)+ Calcd for C17H15N2O 263.1184, found 263.1194.





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