Synthesis of phenylacetic acid

Preparation of phenylacetic acid

Preparation of phenylacetic acid

Preparation of phenylacetic acid

50 g of benzyl cyanide and 150 g of 80% sulphuric acid are placed in a 500ml round-bottomed flask connected by a glass tube bent twice at right angles with a second 500 ml round-bottomed flask fitted with a two-holed cork. The end of the tube is flush with the cork in one hole. Through the second hole passes a vertical glass tube, 50 cm long, dipping just below the surface of 250 ml of water in the flask. In the middle of this tube a large bulb is blown. The whole apparatus is fitted up in a fume cupboard. The mixture is gently heated until small bubbles are seen to rise from the surface of the lower layer of acid. In a few minutes a vigorous reaction begins, the liquid in the flask boils, and a small quantity of benzyl cyanide distils over into the second flask, some of the water in which is forced up into the bulb. When the reaction is over, the flask is again heated for 3 minutes and allowed to cool, its contents solidifying in so doing. The solid residue is washed with cold water, dissolved in hot water, the solution neutralised with sodium carbonate, filtered hot, the filtrate acidified with dilute sulphuric acid, and allowed to stand. The crystals which separate are filtered off, washed with cold water, and recrystallised from hot water. Yield 80%, as colourless thin laminated crystals; soluble in hot water; m.p. 76.5° C; b.p. 262° C;

Systematic organic chemistry, by W. M. Cumming, 240, 1937.

IUPAC Name

2-phenylacetic acid

InChI

InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

InChI Key

WLJVXDMOQOGPHL-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

phenylacetate, phenylacetic acid, phenylacetic acid, ammonium salt, phenylacetic acid, calcium salt, phenylacetic acid, cesium salt, phenylacetic acid, lithium salt, phenylacetic acid, mercury salt, phenylacetic acid, potassium salt, phenylacetic acid, rubidium salt, phenylacetic acid, sodium salt, phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd, sodium phenylacetate

Depositor-Supplied Synonyms

PHENYLACETIC ACID, 2-Phenylacetic acid, Benzeneacetic acid, Phenylethanoic acid, phenylacetate, Benzenacetic acid, alpha-Toluic acid, 103-82-2, Acetic acid, phenyl-, Benzylformic acid, Phenyllacetic acid, Benzylcarboxylic acid, Benzeneacetate, Phenylethanoate, alpha-Toluate, w-Phenylacetate, a-Toluate, a-Toluic acid, Phenylacetic acid (natural), omega-Phenylacetate, Kyselina fenyloctova, Kyselina fenyloctova [Czech], w-Phenylacetic acid, .alpha.-Toluic acid, 2-phenyl-acetic acid, CHEBI:30745, omega-Phenylacetic acid, 2-phenylethanoate, PHENYL-ACETIC ACID, .omega.-Phenylacetic acid, NSC 125718, BRN 1099647, CHEMBL1044, UNII-ER5I1W795A, AI3-08920, FEMA No. 2878, HSDB 5010, WLJVXDMOQOGPHL-UHFFFAOYSA-N, alpha-Tolylic acid, EINECS 203-148-6, NSC125718, SBB058199, NCGC00159477-02, DSSTox_CID_1656, DSSTox_RID_76268, DSSTox_GSID_21656, CAS-103-82-2, Benzeneacetiic acid, organic white solid, Phenylacetate, XIX, 51146-16-8, bmse000220, Epitope ID:116202, AC1L1AI8, SCHEMBL1459, P16621_ALDRICH, METHYL, CARBOXYPHENYL-, P6061_SIGMA, W287806_ALDRICH, W287814_ALDRICH, AC1Q74Z6, ER5I1W795A, BDBM16419, CTK0H5030, HMDB00209, 7188-16-1 (ammonium salt), MolPort-001-002-105, ZINC388462, 114-70-5 (hydrochloride salt), 52009-49-1 (calcium salt), 13005-36-2 (potassium salt), PHENYL(ACETIC ACID-1-13C), Phenylacetic acid_GurudeebanSatyavani, Tox21_113042, Tox21_200533, NSC139637, STK297835, AKOS000291351, Tox21_113042_1, DL-0063, LS-3041, MCULE-6701370784, NSC-125718, NSC-139637, RTC-020466, NCGC00159477-03, NCGC00159477-05, NCGC00258087-01, AJ-20636, AN-24656, AN-43174, BP-11383, BT000138, NCI60_000596, NCI60_002571, OR195993, OR200640, OR288299, AB1003238, DB-003759, FT-0660048, ST45061317, C07086, 28028-EP2269988A2, 28028-EP2270006A1, 28028-EP2270008A1, 28028-EP2272839A1, 28028-EP2272840A1, 28028-EP2275403A1, 28028-EP2275413A1, 28028-EP2287156A1, 28028-EP2292617A1, 28028-EP2295433A2, 28028-EP2301940A1, 28028-EP2305250A1, 28028-EP2305260A1, 28028-EP2305658A1, 28028-EP2308833A2, 28028-EP2308848A1, 28028-EP2311807A1, 28028-EP2311809A1, 28028-EP2311825A1, 28028-EP2314588A1, 79377-EP2298766A1, 79377-EP2305695A2, 79377-EP2305696A2, 79377-EP2305697A2, 79377-EP2305698A2, 4-09-00-01614 (Beilstein Handbook Reference), 3B4-1077, I14-7335, 3B3-024425, 8727557E-AA75-49E9-8E5A-7A2412D71888, InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10

Removed Synonyms

2-phenylacetate, Buphenyl, sodium phenylacetate, Ucephan, 2-Phenylethanoic acid, BENZYLFORMATE, Rhizophora mucronata, |O-phenylacetic acid, PHENYL ACETIC ACID, phenylacetic acid, cesium salt, C8H8O2, CID999, phenylacetic acid, calcium salt, phenylacetic acid, lithium salt, phenylacetic acid, mercury salt, phenylacetic acid, ammonium salt, phenylacetic acid, rubidium salt, phenylacetic acid, potassium salt, +/-(1/2) xEa, PHENYLACETIC ACID, SODIUM SALT, |A-Tolylic acid; Benzeneacetic acid; PAA, |A-(1/4)x+/-(1/2)(1/4)xEa, C025136, phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd, 114-70-5, PA, PAA, PAC, 177985-34-1

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