N-Hydroxyphthalimide → HCID 14647062, compound

HRID 1090474Notes

Reaction equation

HRID 1090474 reaction equation
Br[CH2:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[OH:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]>CN1CCCC1=O>[C:6]1(/[CH:5]=[CH:4]/[CH2:3][CH2:2][O:18][N:19]2[C:20](=[O:29])[C:21]3=[CH:28][CH:27]=[CH:26][CH:25]=[C:22]3[C:23]2=[O:24])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 12585838[(1E)-4-bromo-1-butenyl]benzene

Product 1

HCID 14647062HCID 14647062, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Example 1 was repeated to react 67 g (0.32 mol) of E-4-bromo-1-phenyl-1-butene with 29 g of potassium carbonate (0.21 mol) and 51.9 g of N-hydroxyphthalimide (0.32 mol) in 320 ml of N-methylpyrrolidone. The crude product, precipitated by means of ice-water, was taken up in dichloromethane and washed twice with dilute sodium hydroxide solution. A customary working up gives the product in a 56% yield.

Workup

  1. customThe crude product, precipitated by means of ice-water
  2. washwashed twice with dilute sodium hydroxide solution
  3. customup gives the product in a 56% yield

Sources & evidence

ORD record
ord-85d4f9e8b8c34b03a90dfeeec8148ebd
Source dataset
uspto-grants-1992_01
Patent number
US05081301

Reaction notes

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