Sulfuric Acid → 5-Oxo-2-tetrahydrofurancarboxylic acid

HRID 866533Notes

Reaction equation

HRID 866533 reaction equation
N[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].N([O-])=O.[Na+].OS(O)(=O)=O>O>[C:8]([CH:2]1[O:7][C:5](=[O:6])[CH2:4][CH2:3]1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33032L-Glutamic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 2515245-Oxo-2-tetrahydrofurancarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 200 ml. of water is suspended 29.4 g. (0.2 M) of H.Glu.OH, and a solution of 16.8 g. (0.24 M) of sodium nitrite in 120 ml. of water and 120 ml. of 2N-H2SO4 are simultaneously added dropwise at room temperature over a period of about 90 minutes. The reaction mixture is allowed to stand for 12 hours. The water is distilled off under reduced pressure and hot acetone is added to the residue. The acetone is distilled off from the extract and the oily residue is purified by distillation under reduced pressure. The desired compound is obtained as a distillate between 170.0 and 175.0° C/O 5 mmHg. Yield 14.3 g. (55.0%); melting point: 50° C; optical rotation [α]D27 -11.4° (c=0.77, in 2N-NaOH).

Workup

  1. distillationThe water is distilled off under reduced pressure and hot acetone
  2. additionis added to the residue
  3. distillationThe acetone is distilled off from the
  4. extractionextract
  5. distillationthe oily residue is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-056bb282c10b47af91fffb97027c50e8
Source dataset
uspto-grants-1978_07
Patent number
US04100152

Reaction notes

Loading…