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

HRID 854706Notes

Reaction equation

HRID 854706 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-cfb0f94a6500450aa715dbf5baa7778b
Source dataset
uspto-grants-2007_08
Patent number
US07259271B2

Reaction notes

Loading…