Synthesis of 3-phenylpropionic acid

Preparation of 3-phenylpropionic acid

Preparation of 3-phenylpropionic acid

Preparation of 3-phenylpropionic acid

15 grams of cinnamic acid are dissolved in 5% sodium hydroxide solution (75 ml) with warming. Then the solution is cooled, and freshly prepared 2.5 % sodium amalgam is added slowly in small pieces with efficient stirring. After consumption of about 300-350 g of sodium amalgam alloy, a sample of the solution is treated with hydrochloric acid and then again with sodium hydroxide solution. If this no longer decolorizes permanganate, the whole liquid is decanted from the mercury, which is then washed with a little water. The solution and washings are neutralized with hydrochloric acid, filtered again if necessary, treated with 15 ml of concentrated hydrochloric acid and extracted with ether. The extract is dried with sodium sulfate and the ether is removed by evaporation. The residual oil solidifies when rubbed. The yield amounts to about 12 g, corresponding to 79%. Recrystallization from the water gives pure 3-phenylpropionic acid, which melts at 48.7 ° C.

Die Praxis des organischen Chemikers, Berlin, 1947.

Preparation of 3-phenylpropionic acid by decarboxylation benzylmalonic acid

Preparation of 3-phenylpropionic acid by decarboxylation benzylmalonic acid

Preparation of 3-phenylpropionic acid by decarboxylation benzylmalonic acid

1 g benzylmalonic acid is heated in a wide test-tube in a bath to 180° C. A vigorous evolution of carbon dioxide begins, and continues for about 10 minutes. On cooling the mass solidifies. It is recrystallized from hot water, yielding 3-phenylpropionic acid (hydrocinnamic acid) with melting point 47° C. Yield almost quantitative.

Introduction to the preparation of organic compounds, E. Fisher, 80, 1909

 

IUPAC Name

3-phenylpropanoic acid

InChI

InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)

InChI Key

XMIIGOLPHOKFCH-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CCC(=O)O

MeSH Synonyms

3-phenylpropanoic acid, 3-phenylpropionate, 3-phenylpropionic acid, 3-phenylpropionic acid, sodium salt, beta-phenylpropionate, dihydrocinnamic acid, hydrocinnamic acid

Depositor-Supplied Synonyms

hydrocinnamic acid, 3-Phenylpropanoic acid, 3-phenylpropionic acid, 501-52-0, Benzylacetic acid, Benzenepropanoic acid, Dihydrocinnamic acid, Benzenepropionic acid, BETA-PHENYLPROPIONIC ACID, 3-Phenyl-propionic acid, Phenylpropanoic acid, Phenylpropanoate, Phenylpropionic acid, 3-Phenyl propanoic acid, NSC 9272, CHEMBL851, .beta.-Phenylpropionic acid, PHENYL PROPIONIC ACID, UNII-5Q445IN5CU, FEMA No. 2889, CCRIS 3199, CHEBI:28631, XMIIGOLPHOKFCH-UHFFFAOYSA-N, benzylacetate, hydrocinnamate, EINECS 207-924-5, 3PP, BRN 0907515, AI3-00892, HCI, 3-Phenyl propionic acid, beta-phenylpropionate, Hydrozimtsaeure, Dihydrocinnamate, Benzenepropionate, Hyrocinnamic acid, b-Phenylpropionate, w-Phenylpropanoate, 1ahx, 1tog, 1toi, 1toj, 3-Phenylpropionicacid, 3-Phenylpropionsaeure, omega-Phenylpropanoate, PubChem8185, b-Phenylpropionic acid, w-Phenylpropanoic acid, 3-Phenyl-n-propionate, beta-Phenylpropioic acid, 3-phenyl-propanoic acid, omega-Phenylpropanoic acid, Hydrocinnamic acid (8CI), 3-Phenyl-n-propionic acid, bmse000675, .beta.-Phenylpropanoic acid, AC1L18HU, SCHEMBL3419, ACMC-1AV13, DSSTox_CID_27064, DSSTox_RID_82080, DSSTox_GSID_47064, KSC269K2L, W288918_ALDRICH, 135232_ALDRICH, 5Q445IN5CU, AC1Q758W, 56670_FLUKA, CTK1G9525, HMDB00764, NSC9272, MolPort-000-860-904, BB_NC-2055, NSC-9272, Tox21_302329, ANW-30923, BBL011572, SBB056662, STK286011, AKOS000119624, BS-3829, DB02024, EBD2219941, MCULE-1670073750, RP17362, RTR-023276, NCGC00256189-01, 4CN-1028, AJ-13311, AK-94756, AN-21425, BP-21020, CAS-501-52-0, KB-33158, LS-31175, SC-04862, ST097541, AB1003457, DB-014319, ST2410839, TL8003324, 840-EP2272829A2, 840-EP2275105A1, 840-EP2277867A2, 840-EP2284166A1, 840-EP2287154A1, 840-EP2289891A2, 840-EP2292228A1, 840-EP2292589A1, 840-EP2292590A2, 840-EP2295402A2, 840-EP2295407A1, 840-EP2295413A1, 840-EP2295415A1, 840-EP2295427A1, 840-EP2295436A1, 840-EP2298305A1, 840-EP2298736A1, 840-EP2298742A1, 840-EP2298779A1, 840-EP2301923A1, 840-EP2301928A1, 840-EP2305257A1, 840-EP2305660A1, 840-EP2305667A2, 840-EP2305668A1, 840-EP2305696A2, 840-EP2305697A2, 840-EP2305698A2, 840-EP2305808A1, 840-EP2308833A2, 840-EP2308845A2, 840-EP2308850A1, 840-EP2308872A1, 840-EP2308873A1, 840-EP2308879A1, 840-EP2311455A1, 840-EP2311796A1, 840-EP2311797A1, 840-EP2311798A1, 840-EP2311802A1, 840-EP2311803A1, 840-EP2311815A1, 840-EP2311825A1, 840-EP2311829A1, 840-EP2311836A1, 840-EP2314576A1, 840-EP2314580A1, 840-EP2314581A1, 840-EP2314586A1, 840-EP2316457A1, 840-EP2316827A1, 840-EP2316828A1, 840-EP2316829A1, 840-EP2371814A1, 840-EP2374454A1, FT-0616346, C05629, M-6092, 15228-EP2316832A1, 15228-EP2316833A1, 16418-EP2275401A1, 16418-EP2281563A1, 16418-EP2289890A1, 16418-EP2305646A1, 16418-EP2308868A1, 16418-EP2311842A2, 16418-EP2316459A1, 3-PHENYLPROPIONIC ACID3-Phenyl-propionic acid, 4-09-00-01752 (Beilstein Handbook Reference), 3B4-1067, I01-2033, E76D1F9D-CBB1-4B91-8949-75B4F6F4C481, 3-Phenylpropionic acid; Benzylacetic acid; Hydrocinnamic acid, InChI=1/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11

Removed Synonyms

3-phenylpropionate, 3-phenylpropanoate, PHENYLALANINAL, Cyclohexanepropionic acid, CID107, PHENYLETHYLENECARBOXYLIC ACID, 3-phenylpropionic acid, sodium salt, H0183, C035253, 701-97-3, PHA, TCA

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