Oxalic Acid → HCID 131713518, compound

HRID 1262612Notes

Reaction equation

HRID 1262612 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][C@@H:17]([OH:20])[C@H: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][C@@H:17]([OH:20])[C@H: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 3776IsopropanolHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 131713518HCID 131713518, 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 was 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 recrystallized 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 was 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. customThe resulting white solid was recrystallized twice from isopropyl alcohol
  12. customto yield 13.4 g

Sources & evidence

ORD record
ord-202e0afdfdbf47f4953da4c965571e9d
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

Loading…