Water → Phthalylglycine aldehyde

HRID 606122

Reaction equation

HRID 606122 reaction equation
O.FC(F)(F)C(O)=O.C([O:11][CH:12](OCC)[CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])C>C(Cl)(Cl)Cl>[O:24]=[C:15]1[C:16]2[C:17](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:19])[N:14]1[CH2:13][CH:12]=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 3152862-Phthalimidoacetaldehyde Diethyl Acetal

Product 1

HCID 76201Phthalylglycine aldehydeYield 65.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Water (50 mL) and trifluoroacetic acid (50 mL) were added to a solution of phthalimidoacetaldehyde diethyl acetal (30.0 g, 114 mmol) in chloroform (200 mL), and the reaction mixture was stirred at room temperature for 48 hours. The aqueous layer was separated, adjusted to pH 7 with the addition of sodium carbonate, and extracted with several portions of dichloromethane. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 14.2 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetaldehyde as a white solid.

Workup

  1. customThe aqueous layer was separated
  2. additionadjusted to pH 7 with the addition of sodium carbonate
  3. extractionextracted with several portions of dichloromethane
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef28f501bb744008f701a1198c8f3c7
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Linked notes

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