Reaxys
PubChem
eMolecules
Reactions (23)
Yield
Substances (4)
Citations (27)
Conditions
References
1
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Rx-ID: 3342485 Find similar reactions
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98%
With trichlorophosphate
Maccarone, Emanuele; Cuffari, Giuseppe; Passerini, Amedeo; Raymo, Francisco
Journal of Chemical Research, Miniprint, 1991 , # 9 p. 2401 - 2413 Title/Abstract Full Text Show Details
98%
With trichlorophosphate
T=-5 - 0°C; Inert atmosphere; Hide Experimental Procedure
PIRAMAL LIFE SCIENCES LIMITED; BANDGAR, Babasaheb Pandurang; TOTRE, Jalindar Vasant
Patent: WO2011/121505 A1, 2011 ; Location in patent: Page/Page column 42 ; Title/Abstract Full Text Show Details
8:
Example 82,4,6-Trimethoxy-benzaldehyde2,4,6-Trimethoxy-benzene (40gm, 0.22x103 mmol) was added to dimethylformamide and stirred at a temperature in the range of -5 to 0°C under N2 atmosphere, followed by addition of phosphorus oxychloride (48 gm, 0.5x103 mmol) drop wise over a period of 30-45 minutes. The reaction mixture was stirred for one hour at 0°C, poured over crushed ice followed by saturated sodium carbonate solution. Precipitate obtained was filtered and washed with water to obtain the title compound.Yield: 46 gm (98percent); 1 HNMR (CDCI3): δ 10.35 (s, 1 H), 6.67 (s, 2H), 3.88 (s, 6H), 3.87 (s, 3H); MS: m/e 197 (M+1
).
98%
With trichlorophosphate
Nenikis, Algirdas; Stonius, Sigitas
T=0°C; Vilsmeier-Haack Formylation; 1.75 h;
European Journal of Organic Chemistry, 2015 , vol. 2015, # 28 p. 6359 - 6369 Title/Abstract Full Text View citing articles Show Details
92%
With trichlorophosphate
T=20°C; Vilsmeier Reaction; 16 h;
Huang, Yu; Gan, Haifeng; Guo, Kai
Journal of Chemical Research, 2015 , vol. 39, # 8 p. 458 - 461 Title/Abstract Full Text View citing articles Show Details
91%
With trichlorophosphate
Vilsmeier-Haack Formylation; Inert atmosphere;
Sum, Tze Han; Sum, Tze Jing; Stokes, Jamie E.; Galloway, Warren R.J.D.; Spring, David R.
Tetrahedron, 2015 , vol. 71, # 26-27 p. 4557 - 4564 Title/Abstract Full Text View citing articles Show Details
78%
With trichlorophosphate
T=0°C; 1 h; Inert atmosphere;
Ikawa, Takashi; Kaneko, Hideki; Masuda, Shigeaki; Ishitsubo, Erika; Tokiwa, Hiroaki; Akai, Shuji
Organic and Biomolecular Chemistry, 2015 , vol. 13, # 2 p. 520 - 526 Title/Abstract Full Text View citing articles Show Details
36.9 g
With trichlorophosphate
1.5 h; Ambient temperature;
Sargent, Melvyn V.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982 , p. 403 - 411 Title/Abstract Full Text View citing articles Show Details
101 g
With trichlorophosphate
T=0°C; 1 h; Hide Experimental Procedure
Innochem (Beijing) Technology Co., Ltd.; Chen, Congxi; Tian, Yongjian; Liang, Qiuyan; Bao, Xiaowei
Patent: CN105601604 A, 2016 ; Location in patent: Paragraph 0144; 0145; 0146; 0147; 0148 ; Title/Abstract Full Text Show Details
1.1:Step 1): Preparation of Compound I (2,4,6-trimethoxybenzaldehyde)
100 g of the compound SM (phloroglucinol trimethylether) and 500 ml of DMF were mixed,Ice salt bath cooling to below 0 ,Dropping 201 g (2.2 eq) of phosphorus oxychloride, controlling the temperature below 0 ° C,Canada completed, the following 0 insulation reaction 1h,TLC followed the completion of the reaction; the reaction solution poured into ice water, potassium carbonate solution adjusted to weakly alkaline (pH 8-10), crystallization overnight, filtered to obtain a white solid, dried to 101g product (Compound I) Hydrogen nuclear magnetic resonance (HNMR) spectrum shown in Figure 1.
2
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Rx-ID: 39884141 Find similar reactions
44%
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Stage #1: 1,2,3-trimethoxybenzene With titanium tetrachloride in dichloromethane
T=0°C; 1 h; Inert atmosphere; Stage #2: Dichloromethyl methyl ether in dichloromethane
T=0°C; 0.75 h; Inert atmosphere; regioselective reaction; Hide Experimental Procedure
Ramos-Tomillero, Iván; Paradís-Bas, Marta; De Pinho Ribeiro Moreira, Ibério; Bofill, Josep María; Nicolás, Ernesto; Albericio, Fernando
Molecules, 2015 , vol. 20, # 4 p. 5409 - 5422 Title/Abstract Full Text View citing articles Show Details
3.2. General Formylation Procedure
General procedure: The appropriate benzene derivative (3.2–10.6 mmol) was dissolved in dry DCM (10–20 mL), purged with Ar, and cooled with an ice bath to 0 °C. Next, TiCl4 (2.2 eq.) was added dropwise. The reaction mixture was stirred for 1 h. Afterwards, dichloromethyl methyl ether (1.1 eq.) was added, and the mixture was left to react for a further 45 min. As a reaction quencher, a saturated solution of NH4Cl (25 mL) was added. The mixture was then left for 2 h. The organic layer was separated and washed with 0.1 N HCl solution (3 × 50 mL) and brine (3 × 50 mL). The organic layer was dried over MgSO4 and filtered, and the solvent was evaporated under vacuum to furnish the desired aldehydes (Figure 1). The purified products were homogeneous by HPLC and were characterized and purified by using various physical techniques. A
B
3
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Rx-ID: 41379709 Find similar reactions
A: 12% B: 15%
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Mottweiler, Jakob; Rinesch, Torsten; Besson, Claire; Buendia, Julien; Bolm, Carsten
Green Chemistry, 2015 , vol. 17, # 11 p. 5001 - 5008 Title/Abstract Full Text View citing articles Show Details
With 3C6H12N2*Fe(3+)*3Cl(1-); hydrogen peroxide; acetic acid in water; dimethyl sulfoxide T=100°C; 16 h;
A
B
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4
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Rx-ID: 35445058 Find similar reactions
A: 65% B: 4%
With silver trifluoromethanesulfonate in dichloromethane
T=0°C; 0.25 h; Inert atmosphere;
Ohsawa, Kosuke; Yoshida, Masahito; Doi, Takayuki
Journal of Organic Chemistry, 2013 , vol. 78, # 7 p. 3438 - 3444 Title/Abstract Full Text View citing articles Show Details
5
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With K2OsO2(OH)4; chloramine-T in water; tert-butyl alcohol
0.416667 h; chemoselective reaction; Hide Experimental Procedure
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Rx-ID: 36620458 Find similar reactions
Devari, Shekaraiah; Deshidi, Ramesh; Kumar, Manjeet; Kumar, Arvind; Sharma, Simmi; Rizvi, Masood; Kushwaha, Manoj; Gupta, Ajai Prakash; Shah, Bhahwal Ali
Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6407 - 6410 Title/Abstract Full Text View citing articles Show Details
oxidation of allylic and benzylic alcohol
General procedure: Chloramine-T (0.5 equiv) was added to a solution of K2[OsO2 (OH)4] (3 molpercent) in t-BuOH/H2O (1:1) followed by the addition of alcohol (1.0 mmol) and kept on stirring till completion (confirmed by TLC). The reaction was quenched by adding sodium sulphite(Na2SO3) and stirred for 30 min. The mixture
after extraction with ethyl acetate (twice), usualworkup and purification over silica gel column using Hexane:EtOAc (95:5) afforded pure products.
6
A
B
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Rx-ID: 33465203 Find similar reactions
A: 55% B: 44%
Stage #1: phloroglucinol trimethyl ether With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.5 h; Stage #2: N,N-dimethyl-formamide in tetrahydrofuran; hexane
T=-78 - 20°C; 2 h; Stage #3: methanol Further stages; Hide Experimental Procedure
Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo
Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709 Title/Abstract Full Text View citing articles Show Details
4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF
General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.
7
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8
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Rx-ID: 34041743 Find similar reactions
Bandgar, Babasaheb P.; Hote, Baliram S.; Jalde, Shivkumar S.; Gacche, Rajesh N.
Medicinal Chemistry Research, 2012 , vol. 21, # 10 p. 3006 - 3014 Title/Abstract Full Text View citing articles Show Details
Vilsmeier-Haack Formylation;
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Rx-ID: 30965694 Find similar reactions
89%
9
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide
T=20°C; 2 h; Molecular sieveInert atmosphere;
Huang, Jie; Lebaeuf, David; Frontier, Alison J.
Journal of the American Chemical Society, 2011 , vol. 133, # 16 p. 6307 - 6317 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 30965699 Find similar reactions
Multi-step reaction with 2 steps 1: lithium aluminium deuteride / diethyl ether / 0 - 20 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / 2 h / 20 °C / Molecular sieve; Inert atmosphere View Scheme
Huang, Jie; Lebaeuf, David; Frontier, Alison J.
Journal of the American Chemical Society, 2011 , vol. 133, # 16 p. 6307 - 6317 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 27908504 Find similar reactions
With water
T=37°C; pH=4 - 7.5; Acidic conditions; Hide Experimental Procedure
Colson, Yolonda; Azouz, Solomon; Grinstaff, Mark; Wolinsky, Jesse; Griset, Aaron
Patent: US2008/75718 A1, 2008 ; Location in patent: Page/Page column 44 ; Title/Abstract Full Text Show Details
23:
A sample of the nanoparticles from Example 18 was diluted in buffer at a pH 4, 5, or 7.4 and maintained at 37° C. The diameter of the particles was then measured at regular time intervals using dynamic light scattering (DLS), showing how the particles increased in size over time. Prior to each DLS measurement, the samples were sonicated for 5 seconds to break up aggregates. Particle swelling from 100 nm in diameter to near 1 μm in diameter was observed (see FIG. 9). In addition, the release of free 2,4,6-trimethoxybenzaldehyde was observed using UV/V is spectroscopy at a wavelength of 292 nm, also indicating deprotection of the polymer side groups (see FIG. 10). These particles are useful for controlled release applications as well as for cosmetic applications in which the increase in volume could reduce wrinkles of increase the sized of tissue into which these polymers are injected. A
B
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11
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Rx-ID: 28202322 Find similar reactions
A: 33% B: 22%
With aluminum (III) chloride in chlorobenzene
T=0 - 18°C; 22 h;
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Kantlehner, Willi; Anders, Ernst; Mezger, Jochen; Stoyanov, Edmont V.; Kress, Ralf; Wermann, Kurt; Frey, Wolfgang; Goerls, Helmar
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2008 , vol. 63, # 4 p. 395 - 406 Title/Abstract Full Text View citing articles Show Details
12
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Rx-ID: 11167311 Find similar reactions
77%
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Stage #1: With aluminium trichloride in toluene
T=20°C; 15 h; Stage #2: With water in toluene
T=20°C; 2 h; Further stages.;
Tobisu, Mamoru; Yamaguchi, Seiji; Chatani, Naoto
Organic Letters, 2007 , vol. 9, # 17 p. 3351 - 3353 Title/Abstract Full Text View citing articles Show Details
13
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Rx-ID: 9895372 Find similar reactions
85%
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With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction;
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
14
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Rx-ID: 8966785 Find similar reactions
65%
in sulfuric acid
1 h;
Panda; Parthasarathy
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 7 p. 628 - 631 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 70 percent / NaOH / dioxane; H2O / 4 h / Heating 2: 69 percent / H2SO4 / 1 h View Scheme
Panda; Parthasarathy
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 7 p. 628 - 631 Title/Abstract Full Text View citing articles Show Details
15
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69%
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Rx-ID: 8969686 Find similar reactions
Panda; Parthasarathy
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 7 p. 628 - 631 Title/Abstract Full Text View citing articles Show Details
in sulfuric acid
1 h;
16
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Rx-ID: 15098115 Find similar reactions
Multi-step reaction with 2 steps 1: 68 percent / POCl3 / 6 h / Heating 2: 65 percent / H2SO4 / 1 h View Scheme
Panda; Parthasarathy
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 7 p. 628 - 631 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: 68 percent / POCl3 / 6 h / Heating 2: 70 percent / NaOH / dioxane; H2O / 4 h / Heating 3: 69 percent / H2SO4 / 1 h View Scheme
Panda; Parthasarathy
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 7 p. 628 - 631 Title/Abstract Full Text View citing articles Show Details
A
B
C
17
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Rx-ID: 8748148 Find similar reactions
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With di-tert-butyl peroxide in benzene
24 h; Irradiation; Product distribution;
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McCarroll, Andrew J.; Walton, John C.
Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 12 p. 2399 - 2409 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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18
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Rx-ID: 4773859 Find similar reactions
A: 5.6 % Spectr. B: 2.4 % Spectr. D: 16.0 % Spectr.
With Co(III)W in water; acetic acid
0.5 h; Ambient temperature; Product distribution;
Baciocchi, Enrico; Lanzalunga, Osvaldo; Pirozzi, Bruno
Tetrahedron, 1997 , vol. 53, # 36 p. 12287 - 12298 Title/Abstract Full Text View citing articles Show Details
19
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Rx-ID: 1745236 Find similar reactions
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With water
1.) CH2Cl2, 0 deg C, 0.5 h, 2.) CH2Cl2, 20 deg C, 1 h; Yield given. Multistep reaction;
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Pindur, U.; Flo, C.
Journal of Heterocyclic Chemistry, 1989 , vol. 26, p. 1563 - 1568 Title/Abstract Full Text Show Details
20
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Rx-ID: 7189172 Find similar reactions
Chatterjea; Prasad
Chemische Berichte, 1964 , vol. 97, p. 1252,1254 Full Text Show Details
21
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Rx-ID: 827117 Find similar reactions
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With diethyl ether; trichlorophosphate
anschliessend Behandeln des Reaktionsprodukts mit wss. NaOH;
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Kenyon; Mason
Journal of the Chemical Society, 1952 , p. 4964,4966 Full Text Show Details
22
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Rx-ID: 120998 Find similar reactions
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With hydrogenchloride; zinc(II) chloride; benzene
Reaktion des entstandenen Aldimids mit waessr. Salzsaeure;
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Herzig; Wenzel; Gehringer
Monatshefte fuer Chemie, 1903 , vol. 24, p. 866 Full Text Show Details
23
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Rx-ID: 840152 Find similar reactions
With methanol; sodium methylate
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Herzig; Wenzel; Kerenyi
Monatshefte fuer Chemie, 1903 , vol. 24, p. 861,863 Full Text Show Details