Antoncho posted this a while ago; Post 400120 (https://www.thevespiary.org/talk/index.php?topic=7500.msg40012000#msg40012000)
(Antoncho: "A _possibly_ ABSOLUTELY BEST way of F-C'ing", Chemistry Discourse)
"Looks like all we need to make aceto- and propiophenones from all sorts of stuff is:
a) Tosic acid (make some yourself from toluene and H2SO4)
b) Dean-Stark trap"
Patent US5041616
"I have discovered that aryl ketones may be obtained by heating a carboxylic acid with certain aromatic compounds in the presence of (1) a volatile, organic compound which forms an azeotrope, i.e., a constant boiling mixture, with water and (2) a catalytic amount of an organic sulfonic acid, whereby the water of reaction is removed as an azeotrope from the reaction mixture. "
"The carboxylic acid employed is not critical and may be selected from a wide variety of unsubstituted and substituted, aliphatic, cycloaliphatic and aromatic carboxylic acids containing from 2 to 20 carbon atoms."
"...Phenols and benzenediols, as well as ethers and esters thereof, may be acylated using methanesulfonic and toluenesulfonic acids. In the case of less reactive aromatic compounds such as alkylaromatic compounds, e.g., toluene and xylene, a more acidic sulfonic acid such as a perhaloalkylsulfonic acid, e.g., trifluoromethanesulfonic acid normally is required to achieve satisfactory reaction rates."
EXAMPLE 3
Hydroquinone (11.0 g, 0.1 mole), octanoic acid (30.2 g, 0.21 mole), heptane (110 mL), and methanesulfonic acid (10 mL, 0.14 mole) were heated at reflux (98.degree. C.) for 5 hours in a 300 mL flask equipped with a Dean-Stark trap. During this time, 3 mL of water was collected. The sulfonic acid layer was separated, and the heptane layer was washed once with 50 mL of water and twice with 50 mL portions of saturated, aqueous sodium bicarbonate solution. The mixture was filtered to remove 5 g of product, octanoylhydroquinone octanoate ester, while evaporation of the organic layer gave 17.3 g. The total yield of octanoylhydroquinone was 22.3 g, 94% of theory.
In layman's terms, does mean that all I need to make plain old propiophenone is benzene, propanoic acid and tosic acid?
Thanks,
FF
I apologize, I was wrong on the name of the reagent, not trichloroisocyanuric acid, but cyanuric acid.
Post 382242 (https://www.thevespiary.org/talk/index.php?topic=11582.msg38224200#msg38224200)
(Rhodium: "trichloroisocyanuric acid - cyanuric chloride", Novel Discourse)
Post 383271 (https://www.thevespiary.org/talk/index.php?topic=11582.msg38327100#msg38327100)
(Aurelius: "Cyanuric chloride: -COOH to -COCl/COOR/CONR2", Novel Discourse)
Post 383284 (https://www.thevespiary.org/talk/index.php?topic=11582.msg38328400#msg38328400)
(Aurelius: "Mechanism", Novel Discourse)
Again...
Example of chloroform (and acetic acid) with the haloform reaction:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/chloroform.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/chloroform.html)
MEK reacted with the hypohalite ion, OXl- ,from M+n(OXl-)n, effects the haloform reaction. (halogination, oxidation, cleavage) This cleavage will give you the salt of propionic acid containing a metal cation, M+n, as the counter ion. Also a haloform (thus the name of the reaction) will form. The haloform will be that of the halide, X, such as chloroform formed by the use of a hypochlorite, OCl- ion. (This is also a method for the production of chloroform, iodoform and bromoform for the clandestine chemist.) The haloform is removed and distilled to purify and then placed in a amber, tightly-capped bottle. The aqueous phase is separated, evaporated to give the appropriate salt of propionic acid. This is again acidified with concentrated sulfuric acid:
Post 445659 (missing)
(Aurelius: "Preparing Weak Acids from Salts and Strong Acids", Chemistry Discourse)
and distilled:
Post 445906 (missing)
(Aurelius: "Acid Reagents Physical Properties", Chemistry Discourse)
to obtain the propionic acid. This acid is redistilled for better purity.