12-Bromo-1-dodecanol → N-(12-hydroxydodecyl)phthalimide

HRID 1003309Notes

Reaction equation

HRID 1003309 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K]>CN(C)C=O>[OH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]1[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25]

Participants

4

Reactant 2

HCID 13789512-Bromo-1-dodecanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 18796407N-(12-hydroxydodecyl)phthalimideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 45 g of 12-bromododecanol in 500 ml of dimethylformamide was added 75 g of potassium phthalimide and the mixture was stirred at 100° C. for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was dispersed with water. The crude crystal thus separated out was recovered by filtration and recrystallized from methanol to afford 54 g of the title compound as a crystal.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was dispersed with water
  4. customThe crude crystal thus separated out
  5. filtrationwas recovered by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-524714df53bd4310aa5eb53563652fb5
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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