Water → 2-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1449432

反応式

HRID 1449432 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K].C(OCC)(=O)C.O>CN(C)C=O>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:19]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 779706-Bromo-1-hexanolHCID 24194345Phthalimide potassium salt

生成物 1

HCID 129502192-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-Bromohexan-1-ol (8 g, 44 mmol) and potassium phthalimide (16.4 g, 88 mmol) were heated at 90° C. for two hours in dry N,N-dimethylformamide (50 ml). The mixture was cooled and partitioned between chloroform (150 ml) and water (150 ml). The organic layer washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure to give a yellow liquid. The liquid was left at 4° C. for 72 hours before repartitioning between ethyl acetate (150 ml) and water (150 ml). The organic layer was washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure. Diethyl ether was added and following cooling the solid was removed by filtration. The process was repeated and the liquors were evaporated to give N-(6-hydroxyhexyl)-phthalimide. 1H-NMR: (60 MHz) (CDCl3), δ 7.7 (4H,s), 3.6 (5H,m) and 1.4 (8H,m) ppm

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between chloroform (150 ml) and water (150 ml)
  3. washThe organic layer washed with water (2×150 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give a yellow liquid
  8. washThe organic layer was washed with water (2×150 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customthe filtrate evaporated under reduced pressure
  12. additionDiethyl ether was added
  13. temperaturefollowing cooling the solid
  14. customwas removed by filtration
  15. customthe liquors were evaporated

出典と根拠

ORDレコード
ord-7dbf8d863d50477e9ebbd5cc579ec244
出典データセット
uspto-grants-1997_02
特許番号
US05599587

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