Synthesis of glyceric acid

Preparation of glyceric acid

Preparation of glyceric acid

Preparation of glyceric acid

50 g of glycerol diluted with an equal volume of water are treated in a tall narrow glass cylinder with 50 g of 90% nitric acid, the latter being carefully run in below the surface of the glycerol from a funnel, the neck of which is drawn out into a fine tube, so that two layers are formed. The whole is allowed to stand at the ordinary temperature, till after some little time the liquid becomes homogeneous. The contents of several (six) such cylinders are slowly evaporated on a water bath to a syrup, 2 litres of water are added, and the solution (a) neutralised with lead carbonate and a small quantity of lead oxide. Towards the end of the operation the liquid is boiled and filtered hot. Crude lead glycerate separates on concentrating and cooling the filtrate. The salt which adheres firmly to the side of the vessel is detached by warming. A second crop of crystals slowly separates on concentrating the mother liquors. The finely powdered salt made into a paste with water is treated with hydrogen sulphide in 2.5 g lots, and the solution, filtered from lead sulphide, evaporated on a water bath, when the acid remains as a thick syrup. The aqueous solution (a) may also be worked up for glyceric acid by boiling it with excess of calcium carbonate and filtering hot. The calcium glycerate, which separates on cooling and concentrating, is recrystallised from hot water, suspended in water, and decomposed by treatment with the theoretical quantity of oxalic acid. The clear solution filtered from calcium oxalate is evaporated as above. Yield 80% or 275 g from 300 g of glycerol. Strongly acid syrup, faintly yellow colour; soluble in water, alcohol and acetone; insoluble in ether; decomposes on boiling.

Systematic organic chemistry, by W. M. Cumming, 249, 1937.

IUPAC Name

2,3-dihydroxypropanoic acid

InChI

InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)

InChI Key

RBNPOMFGQQGHHO-UHFFFAOYSA-N

Canonical SMILES

C(C(C(=O)O)O)O

MeSH Synonyms

glyceric acid, glyceric acid, (+-)-isomer, glyceric acid, (R)-isomer, glyceric acid, (S)-isomer, glyceric acid, monopotassium salt

Depositor-Supplied Synonyms

DL-Glyceric acid, GLYCERIC ACID, 2,3-Dihydroxypropanoic acid, 473-81-4, 600-19-1, Polyglyceric acid, 2,3-dihydroxypropans, 2,3-Dihydroxypropanoic acid(20% in water), Propanoic acid, 2,3-dihydroxy-, NSC9227, RBNPOMFGQQGHHO-UHFFFAOYSA-N, 118916-26-0, alpha,beta-Hydroxypropionic acid, glycericacid, Glycerolic acid, Glyceronic acid, Glyceric acid, DL-, (+-)-Glyceric acid, beta-Hydroxylactic acid, ACMC-1AFZW, AC1Q5STB, GLYCERIC ACID, (D), SCHEMBL38462, AC1L19Y2, Propanoic acid,2,3-dihydroxy-, DL-2,3-Dihydroxypropionic Acid, CHEBI:33508, CTK4I9928, MolPort-001-788-307, NSC-9227, EINECS 207-472-9, 8947AB, AR-1D2595, STL268888, AKOS015893067, MCULE-3634533503, RP18860, 43110-90-3 (mono-potassium salt), AK114312, OR026199, OR189165, OR207674, OR292449, Propanoic acid,3-dihydroxy-, (.+-.)-, SC-94999, DB-070797, KB-225260, ST2419200, TC-166640, D0602, FT-0625465, Propanoic acid, 2,3-dihydroxy-, homopolymer, I04-1470, I04-12817, 3B3-023863, 3E9B4D59-D526-4D1F-A6D8-566E4D962CA5, InChI=1/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7, 68084-35-5

Removed Synonyms

glycerate, D-Glyceric acid, UNII-70KH64UX7G, Cyclopentanone-2-carbonitrile, CID752, (2S)-2,3-dihydroxypropanoic acid, 2941-29-9

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