Sulfuric Acid → (1H-Inden-1-yl)acetaldehyde

HRID 1534794Notes

Reaction equation

HRID 1534794 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]=1)#N.[H-].[Cl-].[Na+].[OH:16]S(O)(=O)=O>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:4]1([CH2:3][CH:1]=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 698681H-Indene-3-acetonitrileHCID 166653Hydride

Product 1

HCID 19908307(1H-Inden-1-yl)acetaldehyde

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

3-Cyanomethylindene (3.84 g, 0.025 mol), prepared as described in example 14, was dissolved in a mixture of hexane and THF and stirred under nitrogen at -78°. Dissobutylaluminum hydride (DIBAL) (19.2 ml of a 1.5M solution in toluene; 0.029 mmol) was added and the mixture stirred at ambient temperature 2.5 hours. Saturated sodium chloride solution (220 ml) was added and the mixture stirred another 20 minutes. 5% H2SO4 (90 ml) was added and the solution immediately extracted with ether. The ether layer was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on a silica gel column eluted with 8% Et2O in hexane. The product fraction was evaporated to dryness to provide 2-(1H-indene-1-yl)acetaldehyde.

Workup

  1. addition0.029 mmol) was added
  2. stirringthe mixture stirred at ambient temperature 2.5 hours
  3. stirringthe mixture stirred another 20 minutes
  4. extractionthe solution immediately extracted with ether
  5. dry with materialThe ether layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe residue was chromatographed on a silica gel column
  9. washeluted with 8% Et2O in hexane
  10. customThe product fraction was evaporated to dryness

Sources & evidence

ORD record
ord-d3900c7ee4b147f2b2eeafaeb953ef37
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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