Hydrochloric Acid → 4-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde

HRID 1592440Notes

Reaction equation

HRID 1592440 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][N:9]([OH:12])[C:8]1=[O:13].Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:12][N:9]1[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][CH2:4][CH:3]=[O:2])[C:8]1=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 672723451-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one

Product 1

HCID 865947624-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one (0.753 g, 3.45 mmol) in THF (3 mL) was added 1.0 N HCl (18 mL) and the mixture was stirred at room temperature overnight. The mixture was saturated with solid Na2CO3 (2 g) and extracted with CH2Cl2 (5×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated and provided 0.30 g (51%) of 4-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde as a yellow oil.

Workup

  1. extractionextracted with CH2Cl2 (5×10 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d235a3216198400e884ac474d139e1d7
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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