Bailey, Philip S. published the artcileFurther studies with cis- and trans-¦Â-benzoyl-¦Á- and ¦Â-methylacrylic acids and ¦Â-benzoyl-¦Á-methylenepropionic acid, Related Products of catalysis-chemistry, the publication is Journal of Organic Chemistry (1956), 624-7, database is CAplus.
cf. C.A. 49, 235g. In the preparation of ¦Â-benzoyl-¦Á-methylenepropionic acid (I) by the Friedel-Crafts reaction between C6H6 and itaconic anhydride (II), an acid (III), isomeric with I and cis- (IV) and trans-¦Â-benzoyl-¦Á- (V) and ¦Â-methylacrylic acid (VI), is obtained. The structure of III has been elucidated. Condensation of 50 g. II and 80 cc. C6H6 in 250 cc. CS2 in the presence of 170 g. AlCl3 as described earlier, treatment of the reaction product 2 h. with boiling Ba(OH)2 to hydrolyze I, and steam distillation and acidification of the mixture give 1-oxo-2-indanacetic acid (VII), m. 147-8¡ã (semicarbazone, m. 240-1¡ã; morpholinium salt, m. 124-5¡ã). Refluxing 0.2 g. VII 0.5 h. with 0.8 g. KMnO4 and 0.2 cc. 10% NaOH in 16 cc. H2O, acidifying the mixture with H2SO4, refluxing it another 0.5 h., dissolving the MnO2 with NaHSO3, and extracting with Et2O give o-C6H4(CO2H)2. Adding (4 min.) 2 g. VI to 7.5 g. CrO3 and 6.2 cc. concentrated H2SO4 in 75 cc. boiling H2O, refluxing the mixture 2 min., extracting with Et2O, extracting the washed Et2O solution with dilute NaOH, and acidifying the alk. solution give 47% homophthalic acid, m. 174-6¡ã. Treating 5 g. I 24 h. in 30 cc. morpholine (VIII) and evaporating the solution to 15 cc. give 8.2 g. crystals, m. 100-4¡ã, from which, on extraction with 30 cc. warm Et2O-EtOH (1:1), 2.2 g. ¦Â-benzoyl-¦Á-morpholino-isobutyric acid (IX), m. 118-19¡ã, is obtained (HCl salt, 87%, m. 210-12¡ã); from the insoluble residue 5.5 g. morpholine salt (X) of IX, m. 105-6¡ã, is isolated. Similar results are obtained with IV and V. Treating IX or X with dilute aqueous HCl gives 91% V, m. 109-10¡ã, which is also obtained when IX.HCl is refluxed 1-3 h. in H2O. I is recovered unchanged after treatment with EtOH-HCl. Treating 5 g. I in 50 cc. Et2O 10 min. with 10 cc. VIII gives 66% VIII salt (XI) of I, m. 77-8¡ã, which, on acidification with dilute HCl, gives 60% I, m. 150-4¡ã. Treating XI with an excess of VIII gives 80% IX. On standing, XI is slowly converted into 30% IX. Treating 1 g. VI in 10 cc. Et2O 24 h. with 10 cc. VIII and cooling the mixture with ice gives 83% VIII salt (XII) of ¦Â-benzoyl-¦Á-morpholino-butyric acid (XIII), m. 138-9¡ã, which (6 g.) in 80 cc. H2O adjusted with 5% HCl to pH 5 gives 94% XIII, m. 115-16¡ã. Treating XIII with an excess of VIII gives XII again. XIII of XII in dilute HCl remains stable for several hrs. but when the solution is heated 10-15 min. on a water bath 80-90% VI is formed. An attempt to convert XIII to a dibenzoylmorpholinopropane by a Friedel-Crafts reaction failed.
Journal of Organic Chemistry published new progress about 15732-75-9. 15732-75-9 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ketone, name is 2-Methylene-4-oxo-4-phenylbutanoic acid, and the molecular formula is C11H10O3, Related Products of catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia