The Mechanochemical Fries Rearrangement: Manipulating Isomer Ratios in the Synthesis of p-Hydroxyacetophenone at Different Scales.
Fries rearrangement
ball milling
extrusion
mechanochemistry
para-hydroxyacetophenone
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Apr 2023
13 Apr 2023
Historique:
received:
15
12
2022
medline:
24
1
2023
pubmed:
24
1
2023
entrez:
23
1
2023
Statut:
ppublish
Résumé
Herein, the first mechanochemical Fries rearrangement for the industrially important synthesis of para-hydroxyacetophenone, inside a ball mill and a twin-screw extruder, is presented. Our approach leads to a yield of 62 % in as little as 90 minutes while liquid-assisted grinding can shift the isomer ratio resulting in an excess of the desired para-product. The multigram scale-up by extrusion leads to 61 % yield in only three minutes while completely avoiding solvents. The extrusion temperature can even further be reduced by combining extrusion with a subsequent ageing step.
Identifiants
pubmed: 36683470
doi: 10.1002/chem.202203931
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203931Subventions
Organisme : Bundesministerium für Bildung und Forschung
ID : 03SF0498
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
R. Martin, Org. Prep. Proced. Int. 1992, 24, 369-435.
R. Lin, S. Mitchell, T. Netscher, J. Medlock, R. T. Stemmler, W. Bonrath, U. Létinois, J. Pérez-Ramírez, Catal. Sci. Technol. 2020, 10, 4282-4292.
K. Fries, G. Finck, Chem. Ber. 1908, 41, 4271-4284.
A. H. Blatt, in Organic Reactions, John Wiley & Sons, Ltd, 2011, pp. 342-369.
G. Sartori, R. Maggi, Chem. Rev. 2006, 106, 1077-1104.
I. Jeon, I. Mangion, Synlett 2012, 23, 1927-1930.
F. Jayat, M. J. S. Picot, M. Guisnet, Catal. Lett. 1996, 41, 181-187.
R. Martin, Handbook of Hydroxyacetophenones: Preparation and Physical Properties, Springer, Dordrecht [The Netherlands]; Norwell, MA, 2005.
A. Vogt, H. W. Kouwenhoven, R. Prins, Appl. Catal. A 1995, 123, 37-49.
N. M. Cullinane, B. F. R. Edwards, J. Chem. Soc. 1958, 2926-2929.
“Substance Information - ECHA,” can be found under https://echa.europa.eu/de/substance-information/-/substanceinfo/100.002.548, n.d.
S. L. James, C. J. Adams, C. Bolm, D. Braga, P. Collier, T. Friščić, F. Grepioni, K. D. M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A. G. Orpen, I. P. Parkin, W. C. Shearouse, J. W. Steed, D. C. Waddell, Chem. Soc. Rev. 2012, 41, 413-447.
T. Friščić, C. Mottillo, H. M. Titi, Angew. Chem. Int. Ed. 2020, 59, 1018-1029;
Angew. Chem. 2020, 132, 1030-1041.
J. L. Howard, Q. Cao, D. L. Browne, Chem. Sci. 2018, 9, 3080-3094.
D. Tan, T. Friščić, Eur. J. Org. Chem. 2018, 2018, 18-33.
J. Andersen, J. Mack, Green Chem. 2018, 20, 1435-1443.
W. Pickhardt, M. Wohlgemuth, S. Grätz, L. Borchardt, J. Org. Chem. 2021, 86, 14011-14015.
D. M. Baier, S. Grätz, B. F. Jahromi, S. Hellmann, K. Bergheim, W. Pickhardt, R. Schmid, L. Borchardt, RSC Adv. 2021, 11, 38026-38032.
R. Takahashi, A. Hu, P. Gao, Y. Gao, Y. Pang, T. Seo, J. Jiang, S. Maeda, H. Takaya, K. Kubota, H. Ito, Nat. Commun. 2021, 12, 6691.
M. Đud, A. Briš, I. Jušinski, D. Gracin, D. Margetić, Beilstein J. Org. Chem. 2019, 15, 1313-1320.
D. Tetzlaff, K. Pellumbi, D. M. Baier, L. Hoof, H. S. Barkur, M. Smialkowski, H. M. A. Amin, S. Grätz, D. Siegmund, L. Borchardt, U.-P. Apfel, Chem. Sci. 2020, 11, 12835-12842.
T. Rensch, S. Fabig, S. Grätz, L. Borchardt, ChemSusChem 2022, 15, e202101975.
J. L. Howard, Y. Sagatov, L. Repusseau, C. Schotten, D. L. Browne, Green Chem. 2017, 19, 2798-2802.
J. L. Howard, M. C. Brand, D. L. Browne, Angew. Chem. Int. Ed. 2018, 57, 16104-16108;
Angew. Chem. 2018, 130, 16336-16340.
J. G. Hernández, C. Bolm, J. Org. Chem. 2017, 82, 4007-4019.
Y. Sim, Y. X. Shi, R. Ganguly, Y. Li, F. García, Chem. Eur. J. 2017, 23, 11279-11285.
R. F. Koby, N. D. Schley, T. P. Hanusa, Angew. Chem. 2021, 133, 21344-21348;
Angew. Chem. Int. Ed. 2021, 60, 21174-21178.
T. Seo, N. Toyoshima, K. Kubota, H. Ito, J. Am. Chem. Soc. 2021, 143, 6165-6175.
X. Yang, H. Wang, Y. Zhang, W. Su, J. Yu, Green Chem. 2022, 24, 4557-4565.
V. Martinez, T. Stolar, B. Karadeniz, I. Brekalo, K. Užarević, Nat. Chem. Rev. 2022, 1-15.
N. Cindro, M. Tireli, B. Karadeniz, T. Mrla, K. Užarević, ACS Sustainable Chem. Eng. 2019, 7, 16301-16309.
J. Andersen, J. Mack, Angew. Chem. Int. Ed. 2018, 57, 13062-13065;
Angew. Chem. 2018, 130, 13246-13249.
R. R. A. Bolt, S. E. Raby-Buck, K. Ingram, J. A. Leitch, D. L. Browne, Angew. Chem. Int. Ed. 2022, 61, e202210508.
R. Mocci, E. Colacino, L. D. Luca, C. Fattuoni, A. Porcheddu, F. Delogu, ACS Sustainable Chem. Eng. 2021, 9, 2100-2114.
D. Virieux, F. Delogu, A. Porcheddu, F. García, E. Colacino, J. Org. Chem. 2021, 86, 13885-13894.
K. J. Ardila-Fierro, S. Lukin, M. Etter, K. Užarević, I. Halasz, C. Bolm, J. G. Hernández, Angew. Chem. Int. Ed. 2020, 59, 13458-13462;
Angew. Chem. 2020, 132, 13560-13564.
Q. Cao, J. L. Howard, D. E. Crawford, S. L. James, D. L. Browne, Green Chem. 2018, 20, 4443-4447.
E. Calcio Gaudino, G. Grillo, M. Manzoli, S. Tabasso, S. Maccagnan, G. Cravotto, Molecules 2022, 27, 449.
R. R. A. Bolt, J. A. Leitch, A. C. Jones, W. I. Nicholson, D. L. Browne, Chem. Soc. Rev. 2022, 51, 4243-4260.
D. E. Crawford, C. K. G. Miskimmin, A. B. Albadarin, G. Walker, S. L. James, Green Chem. 2017, 19, 1507-1518.
D. Crawford, J. Casaban, R. Haydon, N. Giri, T. McNally, S. L. James, Chem. Sci. 2015, 6, 1645-1649.
Q. Cao, D. E. Crawford, C. Shi, S. L. James, Angew. Chem. Int. Ed. 2020, 59, 4478-4483;
Angew. Chem. 2020, 132, 4508-4513.
D. E. Crawford, A. Porcheddu, A. S. McCalmont, F. Delogu, S. L. James, E. Colacino, ACS Sustainable Chem. Eng. 2020, 8, 12230-12238.
K. J. Ardila-Fierro, L. Vugrin, I. Halasz, A. Palčić, J. G. Hernández, Chem. Methods 2022, 2, e202200035.
T. Rensch, V. Chantrain, M. Sander, S. Grätz, L. Borchardt, ChemSusChem 2022, 15, e202200651.
D. M. Baier, T. Rensch, D. Dobreva, C. Spula, S. Fanenstich, M. Rappen, K. Bergheim, S. Grätz, L. Borchardt, Chemistry-Methods n.d., n/a, e202200058.
T. Friščić, S. L. Childs, S. A. A. Rizvi, W. Jones, CrystEngComm 2009, 11, 418-426.
L. Gonnet, T. H. Borchers, C. Lennox, J. Vainauskas, Y. Teoh, H. M. Titi, C. J. Barrett, S. G. Koenig, K. Nagapudi, T. Friščić, Faraday Discuss. 2022, 10.1039/D2FD00131D.
K. V. Aken, L. Strekowski, L. Patiny, Beilstein J. Org. Chem. 2006, 2, 1-7.
K. G. Davenport, C. B. Hilton, G. N. Mott, D. L. Keene, Process for Producing 4-Hydroxyacetophenone, 1986, EP0167286 A1.