5-(hydroxymethyl)-2-furaldehyde

R_f 0.55 (ethyl acetate:hexane = 2:1)

Mp.: 28˚C - 32˚C (lit.: 31˚C - 32˚C [6] ). 

IR ν_max (KBr, cm⁻¹): 3405, 3123, 2926, 2851, 1675, 1523, 1397, 

1370, 1334, 1280, 1192, 1023. 

¹H NMR (800 MHz, DMSO-d₆) δ_H 4.51 (d, 2H, J = 6.0 Hz, CHO); 

5.59 (t, 1H, J = 6.0 Hz, OH); 6.61 (d, 1H, J = 3.5 Hz, H-4); 7.50 (d, 1H, J = 3.5 Hz, H-3); 9.55 (s, 1H, CH=O). 

MS(EI): 126 (C₆H₆O₃). EI-MS (rel. int.%): 126(96); 109(10); 97(100); 81(4); 

69(24); 53(9); 41(50); 39(22).

HPLC spectrum

Machine type: Agilent 1260 Infinity LC

Column: Agilent ZORBAX-C18, 4.6mm×150mm

Mobile phase: methanol:water=5:95(0 min)-100:0(15 min), gradient elution

Flow rate: 1 ml min-1

Measurement temperature: room temperature

Detector: UV, wavelength at 278 nm

Sample concentration: 0.5 g L-1

FT-IR spectrum

Measurement type: BRUKER TENSOR 27

Method: KBr pellet

Sample: 10mg HMF:150mg KBr

Wavelength range: 400-4000cm-1

1H-NMR spectrum

Machine type: 400MHz AVANCE III

Sample weight: 30mg

Solvents:CDCl3

13C-NMR spectrum

Machine type: 400MHz AVANCE III

Sample weight: 30mg

Solvent: CDCl3

Frequency: 100.6 MHz

五、The main derivatives of HMF:

Major application fields:

The main application of 5-hydroxymethylfurfual  is as platform chemicals.  Now, HMF  can be  synthesized  fragrance  as a precursor substance.  In addition, HMF can be used in  fine  chemicals   synthesis,  including  pharmaceuticals,  agrochemicals,   macrocycles,  heterocycles,  sugar   derivatives.  In the future,  the main  application  is  to  substitute  oil  to produce  biofuel and  bio-based polymers  as precursor.

...................

Hydroxymethylfurfural
IUPAC name[hide] 5-(hydroxymethyl)-2-furaldehyde
Identifiers
CAS number	67-47-0
ChemSpider	207215
KEGG	C11101
ChEBI	CHEBI:412516
ChEMBL	CHEMBL185885
Jmol-3D images	Image 1
SMILES [show]
InChI [show]
Properties
Molecular formula	C6H6O3
Molar mass	126.11 g/mol
Density	1.29 g/cm3
Melting point	30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point	114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
λmax	282 nm[1]
Related compounds
Related furan-2-carbaldehydes	Furfural Methoxymethylfurfural
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com

The First Synthesis of Sessiline

Sessiline
[5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde 

5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde

http://file.scirp.org/Html/4-1020299_52662.htm

Scheme 4. The synthesis of sessiline (1).

Sessiline (1)

200 mg (1.98 mmol) 5-hydroxypyrrolidin-2-one (2) and 800 mg (6.34 mmol) 5‑hydroxymethylfurfural (3) were stirred at 60˚C under neat conditions for 1 hour. Then the reaction mixture was diluted with 1 - 2 ml dichloro- methane, filtered, the solid washed with 3 × 2 ml dichloromethane, and air-dried with suction. 225 mg (54%) pure 1 was obtained as colourless crystals. R_f 0.47 (acetone:hexane = 2:1).
Mp.: 169˚C - 172˚C (lit.: 171˚C - 172˚C [1] ).

IR ν_max(KBr, cm⁻¹): 3321, 3176, 3117, 2965, 2896, 2863, 2790, 2763, 1772, 1709, 1666, 1531, 1463, 1412, 1389, 1338, 1284, 1276, 1262, 1250, 1208, 1201, 1177, 1096, 1062, 1030, 1007.

¹H NMR (400 MHz, DMSO-d₆) 
δ_H 1.86 - 1.95 (m, 1H, H_x-4’); 
2.01 - 2.10 (m, 1H, H_x-3’); 
2.16 - 2.34 (m, 2H, H_y-4’, H_y-3’); 
4.49 + 4.58 (AB, 2 × 1H, J_gem = 13.2 Hz, CHO); 
5.02 (m, 1H, H-5’);
6.73 (d, 1H, J = 3.4 Hz, H-4); 
7.51 (d, 1H, J = 3.4 Hz, H-3); 
8.80 (s, 1H, NH); 
9.58 (s, 1H, CH=O). 





¹³C NMR (100 MHz, DMSO-d₆) 
δ_C 27.5 (C-4’); 
27.9 (C-3’); 
60.3 (CH₂O); 
85.2 (C-5’); 
111.8 (C-4); 
123.9 (C-3); 
152.2 (C-2); 
157.7 (C-5); 
177.6 (CON); 
178.3 (CH=O). 

HRMS: 210.07605 (C₁₀H₁₂NO₄; calc. 210.07608). 

ESI-MS-MS (cid=65) (rel. int.%): 192(100); 164(8); 126(2); 109(4).

International Journal of Organic Chemistry
Vol.04 No.05(2014), Article ID:52662,4 pages
10.4236/ijoc.2014.45033

The First Synthesis of Sessiline

Viktor Ilkei¹, Kornél Faragó¹, Zsuzsanna Sánta², Miklós Dékány², László Hazai¹, Csaba Szántay Jr.², Csaba Szántay¹, György Kalaus^1*

¹Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary

²Gedeon Richter Plc, Budapest, Hungary

Email: ^*kalaus@mail.bme.hu

Copyright © 2014 by authors and Scientific Research Publishing Inc.

This work is licensed under the Creative Commons Attribution International License (CC BY).

http://creativecommons.org/licenses/by/4.0/

Budapest University of Technology and Economics
Budapesti Műszaki és Gazdaságtudományi Egyetem
Latin: Universitas Budapestinensis Scientiarum Technicarum et Oeconomicarum

The "K", central building looking from the river Danube before its renovation

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary









budapest















central market budapest









DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com

(±)-Methyl 2-[hydroxy(2-nitrophenyl)methyl]prop-2-enoate

¹H NMR (500 MHz, CDCl₃):  
δ 7.94 (dd, J 1.2/8.2 Hz, 1H), 
7.78 (d, 1H, J 7.9 Hz), 
7.61-7.67 (m, 1H), 
7.41-7.48 (m, 1H), 
6.36 (s, 1H), 
6.20 (s, 1H), 
5.72 (s, 1H), 
3.73 (s, 3H), 
3.08 (s, 1H, OH);

¹³C NMR (125 MHz, CDCl₃):  
δ 166.3, 
148.2, 
140.7, 
136.0, 
133.4, 
128.8, 
128.6, 
126.4, 
124.5, 
67.6, 
52.1;

(±)-Methyl 2-[hydroxy(2-nitrophenyl)methyl]prop-2-enoate (3): 92% yield, pale yellow oil; IR (film) ν_max/cm^-1: 3469, 1716, 1630, 1528, 1352;  

¹H NMR (500 MHz, CDCl₃): δ 7.94 (dd, J 1.2/8.2 Hz, 1H), 7.78 (d, 1H, J 7.9 Hz), 7.61-7.67 (m, 1H), 7.41-7.48 (m, 1H), 6.36 (s, 1H), 6.20 (s, 1H), 5.72 (s, 1H), 3.73 (s, 3H), 3.08 (s, 1H, OH);

¹³C NMR (125 MHz, CDCl₃): δ 166.3, 148.2, 140.7, 136.0, 133.4, 128.8, 128.6, 126.4, 124.5, 67.6, 52.1; 

HRMS (ESI TOF) 

Calcd. for C₁₁H₁₁NO₅[M + Na⁺]: 260.0529. Found: 260.0530.

J. Braz. Chem. Soc. vol.22 no.8 São Paulo Aug. 2011

http://dx.doi.org/10.1590/S0103-50532011000800022

http://www.scielo.br/scielo.php?pid=S0103-50532011000800022&script=sci_arttext 


 your cock will teach you nmr







DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com