Julia, Marc published the artcileOrientation of the acid opening of acid-alcohols and substituted cyclopropanediols, Computed Properties of 15732-75-9, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1967), 264(3), 330-2, database is CAplus.
The cyclopropane ring-opening procedure (CA 63, 2914c) was used to prepare a number of unsaturated branched- and straight-chain compounds containing OH and CO2H groups. BzCH2C(:CH2)CO2H was isomerized in the presence of NEt3 to BzCH:CMeCO2R(I, R = H), m. 110¡ã, which was methylated with CH2N2 to I (R = Me), b0.01 120-5¡ã. I (R = Me) treated with Corey’s reagent (C. and Chaykovsky, CA 62, 12994c) gave 5% cis-II (R = Me) and 95% trans-II (R = Me), 2,4-dinitrophenylhydrazone m. 145-7¡ã. Saponification of the mixture gave homogeneous (thin layer chromatography) trans-II (R = H), m. 146-7¡ã, the structure of which was confirmed by N.M.R. spectroscopy. Reduction of II (R = H) by KBH4 gave the OH-acid (III), m. 142-4¡ã, which was treated with 48% aqueous HBr at room temperature to give a product shown to be the branched acid trans-PhCH:CHCMe(CH2Br)CO2H (IV) by N.M.R. Reduction of IV by LiAlH4 gave trans-PhCH:CHCMe2CH2OH (V), b0.4 105-6¡ã; phenylurethane m. 108-9¡ã. Catalytic hydrogenation of V gave the corresponding saturated alc. b0.8 118-19¡ã, the structure of which was confirmed by comparison with the compound prepared from Et methylmalonate by alkylation with PhCH2CH2Br, reduction to the glycol m. 90-1¡ã, conversion to the bromohydrin and reduction with LiAlH4 to the saturated alc.; 3,5-dinitrobenzoate m. 94-5¡ã. Reduction of trans-II (R = H) with LiAlH4 gave the diol (VI), m. 99-100¡ã, which on treatment with 48% aqueous HBr gave PhCH:CHCMe (CH2Br)CH2OH (VII), converted to V by LiAlH4. Treatment of VII with Ac2O in pyridine gave the monoacetate but with AcOH and AcOK gave the diacetate, saponification of which gave the diol, PhCH:CHCH2CMe(OH)CH2OH which could also be prepared by treatment of VI with cold 3.6N H2SO4. trans-PhCH:CHCH2CMe2CO2Me, m. 103-5¡ã, prepared from PhCH:CHCH2CN by methylation with MeI in the presence of NaNH2 in PhMe and saponification of the intermediate PhCH:CHCMe2CN, was used as an N.M.R. reference. Similarly, PhCH:CHCH2CMe(OH)CO2Me was used and prepared by the action of PhCH:CHMe on Me pyruvate.
Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques 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, Computed Properties of 15732-75-9.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia