Ethanol → Ethyl 2-bromo-9-phthalimidononanoate

HRID 980622Notes

Reaction equation

HRID 980622 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH2:29](O)[CH3:30]>O>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])[C:3]([O:5][CH2:29][CH3:30])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13622643HCID 13622643, compound

Product 1

HCID 13622534Ethyl 2-bromo-9-phthalimidononanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 50 ml of ethanol is dissolved 6.8 g of 2-bromo-9-phthalimidononanoic acid, and 5 ml of conc. sulfuric acid is added to the solution. After the solution is left standing overnight, the solution is diluted with 100 ml of water and extracted with 200 ml of ethyl acetate. The ethyl acetate layer is washed with 50 ml of aqueous sodium bicarbonate solution and 50 ml of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily substance is purified by silicagel column chromatography (hexane:ethyl acetate=6:1) to give 6.3 g of ethyl 2-bromo-9-phthalimidononanoate as a colorless oil.

Workup

  1. additionis added to the solution
  2. waitAfter the solution is left
  3. extractionextracted with 200 ml of ethyl acetate
  4. washThe ethyl acetate layer is washed with 50 ml of aqueous sodium bicarbonate solution and 50 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily substance is purified by silicagel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-089dcaa928024537950e002c8ff7d50c
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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