Rapson, Wm. Sage published the artcileSynthesis of substances related to the sterols. VII, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Journal of the Chemical Society (1935), 1533-43, database is CAplus.
Et 1-methyl-¦¤2-cyclopentene-1-carboxylate (I), b13 70-1¡ã, results from the HO ester and P2O6 in C6H6; the acid b14 110¡ã. Reduction of the Et ester gives 70% of 1-methyl-¦¤2-cyclopentenyl-1-carbinol (II), b760 162-5¡ã (p-nitrobenzoate, m. 67¡ã); PCl5 in petr. ether gives the chloride, b18 40-56¡ã, which does not condense with AcCHNaCO2Et in EtOH or C6H6. Dehydration of II with KHSO4 gives a dihydrotoluene(?), b. 112-13¡ã. Electrolytic reduction of 35 g. of m-MeOC6H4CHO (4 amps., c. d., 0.025 amp./sq. cm.) for 3 hrs. gives 20 g. m-MeOC6H4CH2OH (III) and 9 g. of 3,3′-dimethoxyhydrobenzoin ¦Á,¦Á’-di-Me ether, m. 112-13¡ã. III was converted through the chloride and nitrile to Et m-methoxyphenylacetate, which was reduced with Na and EtOH to ¦Â-m-methoxyphenylethyl alc., b12 135-7¡ã; the chloride, b14 128-30¡ã, reacts sluggishly with AcCHNaCO2Et; Et ¦Â-m-methoxyphenylethylacetoacetate b2 180¡ã; hydrolysis gives ¦Ã-m-methoxyphenylpropyl Me ketone, b19 168¡ã (semicarbazone, m. 109¡ã); condensation with I did not give a pure ¦Â-diketone. The K salt of Et trans-cyclopentane-1-carboxylate-2-cyanoacetate and PhCH2Ch2Br give Et ¦Á-cyano-¦Á-(trans-2-carbethoxycyclopentyl)-¦Ã-phenylbutyrate, b1 195-200¡ã; hydrolysis with concentrated HCl (boiling 30 hrs.) gives ¦Á-cyano-¦Á-(trans-2-carboxycyclopentyl)-¦Ã-phenylbutyric acid, m. 210¡ã (decomposition); boiling with H2SO4 and AcOH gives ¦Á-(trans-2-carboxycyclopentyl)-¦Ã-phenylbutyric acid, m. 160-1¡ã; the trans-anhydride, m. 112¡ã, on heating at 250¡ã for 15 min., gives the cis-anhydride, which did not crystallize; the cis-acid m. 133¡ã. The trans-acid with H2SO4 gives 1-keto-2-(trans – 2′ – carboxycyclopentyl) – 1,2,3,4 – tetrahydronaphthalene, m. 164-5¡ã; heating with Ac2O and AcONa and decomposition of the anhydride gives the cis-isomer, m. 155-6¡ã. The Me ester of the trans-acid m. 45¡ã; this did not react with BrCH2CO2Et and Zn. Both acids react with SOCl2 in CHCl3 to yield the trans- and cis- forms of 1-hydroxy – 2 – (2′ – carboxycyclopentyl) – 3,4 – dihydroxynaphthalene lactone, m. 162¡ã and 66¡ã, resp. The transform, monoclinic needles elongated along a, with the faces {021}, {100} developed; the dimensions of the unit cell are a = 8.2, b = 23.4, c = 13.6, ¦Â = 68¡ã; with a density of about 1.315, the number of mols. in the cell is 8; the cis-form crystallizes in triclinic plates, a = 7.27, b = 16.75; d. (001) = 11.0, ¦Ã = 75¡ã; d. 1.267, number of mols. in the unit cell, 4. Catalytic reduction of the trans-lactone yields 2-(2′-trans-carboxycyclopentyl)-1,2,3,4-tetrahydronaphthalene, m. 107¡ã. Et cyclopentan-2-one-1-carboxylate in PCl5 in light petroleum gives Et 2-chloro-¦¤1-cyclopentene-1-carboxylate, b12 95-8¡ã, and a small quantity of the acid, m. 115-16¡ã; this ester did not condense with AcCHNaCO2Et or CHNa(CO2Et)2. m-HOC6H4CHO and PhCH2Cl with Na give m-benzyloxybenzaldehyde, b20 215-18¡ã, m. 54¡ã; hippuric acid and Ac2O give m-methoxybenzylidenephenylisoxazolone, yellow, m. 129¡ã; hydrolysis gives m-benzyloxyphenylpyruvic acid, m. 145¡ã but it decomposes on keeping; alk. H2O2 gives m-benzyloxyphenylacetic acid (IV), m. 126¡ã. Since debenzylation could not be avoided in further work methoxylated intermediates were used. The dry Na salt of IV, 6,3-O2N-(MeO)C6H3CHO (V) and Ac2O, heated on the water bath for 24 hrs., give 2-nitro-5-methoxy-¦Á-(m-benzyloxyphenyl)cinnamic acid, pale yellow, m. 148¡ã; 2-NH2 derivative, m. 137¡ã. m-MeOC6H4CH2CO2Na, V and Ac2O give 2-nitro-5-methoxy-¦Á-(m-methoxyphenyl)cinnamic acid, yellow, m. 148¡ã; 2-NH2 derivative, m. 185¡ã; the diazo reaction gives 63% of a mixture of 44% 2,7-dimethoxyphenanthrene-9-carboxylic acid, pale yellow, m. 265¡ã, and 56% of the 2,5-isomer, pale yellow, m. 191¡ã. Decarboxylation gives 2,7-dimethoxyphenanthrene and the 2,5-isomer, m. 117¡ã (picrate, orange-red, m. 154-6¡ã). 2,5-Dihydroxyphenanthrene, m. 180¡ã; di-Ac derivative, m. 144¡ã. In the preparation of ¦Â-2-hydroxy-1-naphthylethyl Me ketone a by-product is 2-methyl-5,6-(1,2-naphtho)-¦Ã-pyran, b16 190¡ã, m. 44-5¡ã. The K derivative of Et cyclopentanonecarboxylate and octyl bromide, boiled 7 hrs. in C6H4Me2, give Et 1-octylcyclopentan-2-one-1-carboxylate, b1 157-65¡ã (85% yield) (semicarbazone, m. 117¡ã); hydrolysis with Ba(OH)2 gives ¦Á-octyladipic acid, m. 74¡ã, and 2-octylcyclopentanone, b11 135-8¡ã (semicarbazone, m. 183¡ã); reduction of the ketone yields 2-octylcyclopentanol, b23 161¡ã, b8 140¡ã; bromide, b8 135-40¡ã. Octyl-¦¤1-cyclopentene and MeO2CCH2CH2COCl with SnCl2 or AlCl3 give 2-(¦Â-carbomethoxypropionyl)-1-octyl-¦¤1-cyclopentene, b1 173-7¡ã, nD15 1.4818. Work of R. Hirt on cyclopentanone-2-¦Â-propionic acid is described. Refluxing the acid with AcCl gives the enolic lactone, b17 116-7¡ã; cyclopentanol-2-¦Â-propionic acid lactone, b18 138-9¡ã. PhCH2CH2CH2Ac and 85% H2SO4 at 0¡ã give 74% of 1-methyl-3,4-dihydronaphthalene, b14 107-8¡ã.
Journal of the Chemical Society published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Recommanded Product: 2-(3-(Benzyloxy)phenyl)acetic acid.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia