Water ethanol → HCID 54676503, compound

HRID 2296345Notes

Reaction equation

HRID 2296345 reaction equation
C([O:3][C:4](=O)[C:5](=[O:21])[CH:6]([C:19]#[N:20])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])C.C([OH:25])C.O>CS(O)(=O)=O>[OH:21][C:5]1[C:4](=[O:3])[NH:20][C:19](=[O:25])[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 19096565Water ethanolHCID 54347591HCID 54347591, compound

Product 1

HCID 54676503HCID 54676503, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

1 G. of the 3-cyano-2-oxopentadecanoic acid ethyl ester is dissolved in 5 ml of methanesulfonic acid and the mixture allowed to stand overnight at room temperature. The reaction mixture is worked up by first pouring into ethanol-water (20 ml ethanol--5 ml water). After standing for several hours, the ethanol is removed by evaporation. The aqueous acidic residue is diluted further with water and then extracted with chloroform. The chloroform solution is then washed well with water, dried and evaporated to give the desired 3-hydroxy-4-(n-dodecyl)-3-pyrroline-2,5-dione. Recrystallization from hexane or cyclohexane provides pure 3-hydroxy-4-(n-dodecyl)-3-pyrroline-2,5-dione, mp 108°-109° C.

Workup

  1. waitAfter standing for several hours
  2. customthe ethanol is removed by evaporation
  3. additionThe aqueous acidic residue is diluted further with water
  4. extractionextracted with chloroform
  5. washThe chloroform solution is then washed well with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-9d8e4fc06ec24c3d940c9152d05a045b
Source dataset
uspto-grants-1984_01
Patent number
US04428959

Reaction notes

Loading…