Ethanol → HCID 13897406, compound

HRID 1464009Notes

Reaction equation

HRID 1464009 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[CH2:14]([NH2:18])[CH2:15][CH2:16][CH3:17].C(O)C.O>C(OCC)(=O)C.C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[O:13])[N:18]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6](=[O:8])[C:5]2=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8007ButylamineHCID 118814-Hydroxyphthalic acid

Product 1

HCID 13897406HCID 13897406, compound

Reagents, catalysts & solvents 1

HCID 21583983Benzene ethyl acetateSolvent

Procedure

In a 250-ml round bottom flask were placed 20.5 g (112.6 mmols) of 4-hydroxyphthalic acid, 8.2 g (112.6 mmols) of n-butylamine and 100 ml of absolute ethanol. After mixing, the resulting mixture generated heat gently. The mixture was sufficiently stirred until the solids were completely dissolved. The alcohol was distilled off under reduced pressure, after which the viscous liquid thus obtained was heated at 180° C. for about 3 hours with continuous extraction of water. After cooling, the residue was solidified. The solidified residue was dissolved in an ethyl acetate-benzene (1:1 by volume) mixed solvent, and the resulting solution was washed with water, an aqueous sodium carbonate solution and then water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and then cooled to obtain powder crystals having a slightly yellowish white color. The crystals were collected by suction filtration and dried. Yield: 18.5 g (75%), m.p. 126°-127° C. The product was determined to be 4-hydroxy-N-n-butylphthalimide by investigation of its structure by NMR and infrared absorption spectrum.

Workup

  1. customIn a 250-ml round bottom flask were placed
  2. additionAfter mixing
  3. temperaturethe resulting mixture generated heat gently
  4. dissolutionwere completely dissolved
  5. distillationThe alcohol was distilled off under reduced pressure
  6. customafter which the viscous liquid thus obtained
  7. temperatureAfter cooling
  8. additionmixed solvent
  9. washthe resulting solution was washed with water
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. temperaturecooled
  13. customto obtain powder crystals
  14. filtrationThe crystals were collected by suction filtration
  15. customdried
  16. customabsorption spectrum

Sources & evidence

ORD record
ord-048caacb18bf4dc7bb51f838cca33906
Source dataset
uspto-grants-1994_04
Patent number
US05302725

Reaction notes

Loading…