Hydrochloric Acid → 2-(4,5-Dihydroxypentyl)isoindole-1,3-dione

HRID 1245775Notes

Reaction equation

HRID 1245775 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:4][O:3]1.Cl>C1COCC1>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219154692-[3-(2,2-Dimethyl[1,3]dioxolan-4-yl)propyl]isoindole-1,3-dione

Product 1

HCID 219154622-(4,5-Dihydroxypentyl)isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[3-(2,2-dimethyl[1,3]dioxolan-4-yl)propyl]isoindole-1,3-dione (1.65 g, 5.70 mmol) in THF (20 mL) at room temperature was added 2N HCl solution (15 mL, 30 mmol) in one portion and the resulting mixture was stirred at room temperature for two hours and then evaporated in vacuo to half of the initial volume. The residue was saturated with NaCl and extracted with ethyl acetate. The organic phase was dried by anhydrous magnesium sulfate. Filtration and concentration in vacuo afforded a colourless oil.

Workup

  1. customevaporated in vacuo to half of the initial volume
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried by anhydrous magnesium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customafforded a colourless oil

Sources & evidence

ORD record
ord-b656477969534e7394cb1ab8027023a7
Source dataset
uspto-grants-2006_10
Patent number
US07125904B2

Reaction notes

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