4-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]benzaldehyde → HCID 57111979, compound

HRID 2260714Notes

Reaction equation

HRID 2260714 reaction equation
[C:1]1(=O)[N:5]([CH2:6][CH2:7][O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12>C(O)(=O)C.[Zn]>[C:4]1(=[O:17])[C:3]2[C:2](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:1][N:5]1[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 128106414-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]benzaldehyde

Product 1

HCID 57111979HCID 57111979, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

4-(2-Phthalimidoethoxy)benzaldehyde (6.8 g) was dissolved in glacial acetic acid (70 ml) at 60° C. Powdered zinc (9.1 g) was added, and the mixture heated at reflux and stirred vigorously for 18.25 hours before being filtered whilst hot, and allowed to cool to room temperature. The acetic acid was evaporated and the resulting gum dissolved in methanol (75 ml). Sodium hydroxide solution (10% w/v; 75 ml) was added, and the mixture stirred for 2 hours at room temperature, diluted with water (1 l), acidified to pH4 with hydrochloric acid, and then continuously extracted with dichloromethane for 3 hours. The dichloromethane layer was evaporated and the residue chromatographed on silica gel using 1.5% methanol in dichloromethane to afford the title compound, mp 106°-107° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. filtrationbefore being filtered whilst hot, and
  4. customThe acetic acid was evaporated
  5. dissolutionthe resulting gum dissolved in methanol (75 ml)
  6. additionSodium hydroxide solution (10% w/v; 75 ml) was added
  7. stirringthe mixture stirred for 2 hours at room temperature
  8. additiondiluted with water (1 l)
  9. extractioncontinuously extracted with dichloromethane for 3 hours
  10. customThe dichloromethane layer was evaporated
  11. customthe residue chromatographed on silica gel using 1.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7b621dd47aa54f478582950c68f81a41
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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