Oxalic Acid → HCID 131714650, compound

HRID 1381235Notes

Reaction equation

HRID 1381235 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].[CH2:13]([N:15]1[CH2:19][CH:18]2[O:20][CH:17]2[CH2:16]1)[CH3:14].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].C(O)(C)C>O>[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[CH2:13]([N:15]1[CH2:16][CH:17]([OH:20])[CH:18]([O:10][C:9]2[CH:11]=[CH:12][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=2[O:7][CH3:8])[CH2:19]1)[CH3:14].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[CH2:13]([N:15]1[CH2:16][CH:17]([OH:20])[CH:18]([O:10][C:9]2[CH:11]=[CH:12][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=2[O:7][CH3:8])[CH2:19]1)[CH3:14]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 2214AcetovanilloneHCID 3776Isopropanol2×HCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 131714650HCID 131714650, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A mixture of 17.0 g. (0.15 mole) of acetovanillone and 1-ethyl-3,4-epoxypyrrolidine and 3 drops of water was heated on a steam bath overnight. The mixture was dissolved in 250 ml. of methylene chloride and extracted with three 150-ml. portions of 5% sodium hydroxide and one 100-ml. portion of water. The methylene chloride layer wad dried over anhydrous sodium sulfate and concentrated to give 19.0 g. crude oil. This oil was chromatographed on 400 g. of silica gel. The desired product was eluted with acetone. The fractions were concentrated to give 14.0 g. of oil which was treated with oxalic acid in isopropyl alcohol. The resulting white solid was recrystllized twice from isopropyl alcohol to yield 13.4 g. (24%) of sesquioxalate, m.p. 121°-3° C.

Workup

  1. additionA mixture of 17.0 g
  2. dissolutionThe mixture was dissolved in 250 ml
  3. extractionof methylene chloride and extracted with three 150-ml
  4. dry with materialThe methylene chloride layer wad dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give 19.0 g
  7. customThis oil was chromatographed on 400 g
  8. washThe desired product was eluted with acetone
  9. concentrationThe fractions were concentrated
  10. customto give 14.0 g
  11. customto yield 13.4 g

Sources & evidence

ORD record
ord-33f6449125e54105bca81b774c4b200d
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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