Horii, Zenichi published the artcileItaconic acid in organic chemistry. I. Synthesis of 2-methyl-1,4-naphthoquinone (menadione), Category: catalysis-chemistry, the publication is Pharmaceutical Bulletin (1957), 82-4, database is CAplus and MEDLINE.
The easy availability of itaconic acid (I) led to its use in the synthesis of the title compound (II). The anhydride of I was converted by the Friedel-Crafts reaction with C6H6 and AlCl3 to BzCH:CMeCO2H (Dixon, et al., C.A. 44, 1516a), which (4 g.) refluxed 24 hrs. with amalgamated Zn (from 16 g. mossy Zn and 1.6 g. HgCl2) in 14 cc. concentrated HCl, 6 cc. H2O, 8 cc. PhMe, and 0.4 cc. AcOH, plus 4 cc. addnl. concentrated HCl each 6 hrs., cooled, the aqueous layer extracted with ether, and the extract distilled underwent the Clemmensen reduction to 1.7 g. Ph(CH2)2CHMeCO2H (III), b3 138-40¡ã. III was also prepared by the catalytic hydrogenation of I to methylsuccinic acid according to D., et al. (loc. cit.), whose anhydride was converted to BzCH2CHMeCO2H, thence to III, and finally to 3,4-dihydro-2-methyl-1(2H)-naphthalenone (IV), all according to Alexander and Mudrak (C.A. 44, 10693i). IV (6 g.) in 60 cc. AcOH oxidized by 12 g. CrO3 in 60 cc. 80% AcOH at such a rate as to keep the temperature below 20¡ã, the mixture kept 36 hrs. at room temperature, and poured into ice H2O yielded 1.8 g. II, m. 104¡ã. Or, IV (14.7 g.) in 200 cc. ether treated gradually below 5¡ã with 16 g. Br, stirred 1.5 hrs., and worked up as usual yielded 17.5 g. 2-Br derivative of IV, m. 66¡ã, and this (1 g.) refluxed 30 min. with 2.5 g. 2,4,6-collidine yielded 0.5 g. 2-methyl-1-naphthol (V), m. 61¡ã. V (1 g.) in 10 cc. AcOH oxidized below 20¡ã by the gradual addition of 1.2 g. CrO3 in 80% AcOH, kept 48 hrs., and poured into ice H2O yielded 0.4 g. II. The structure of II was confirmed by reductive acetylation (Fieser, et al., C.A. 34, 4132) with AcONa, Zn dust, AcOH, and Ac2O to 1,4,2-(AcO)2C10H5Me, m. 112¡ã.
Pharmaceutical Bulletin published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Category: catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia