Water → N-8-(1-naphthyloxy)octylphthalimide

HRID 2118658Notes

Reaction equation

HRID 2118658 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K].O>CN(C=O)C>[C:11]1([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:25]2[C:24](=[O:26])[C:23]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]3[C:21]2=[O:31])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 139572731-(1-Naphthyloxy)-8-chlorooctaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 13520543N-8-(1-naphthyloxy)octylphthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.5 g of 1-chloro-8-(1-naphthyloxy)octane and 8.4 g of potassium phthalimide were taken up in 50 ml DMF and the resulting solution was heated at 140° for 3 hours. The reaction solution was then poured into water and extracted with dichloromethane. The extract was washed, dried and evaporated and the residue was crystallized from acetone/hexane to afford the intermediate N-[8-(1-naphthyloxy)octyl]phthalimide mp 63°-64°.

Workup

  1. temperaturethe resulting solution was heated at 140° for 3 hours
  2. extractionextracted with dichloromethane
  3. washThe extract was washed
  4. customdried
  5. customevaporated
  6. customthe residue was crystallized from acetone/hexane

Sources & evidence

ORD record
ord-6df8c19935ba486f90e1b4e11125b7b7
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

Loading…