Acetone → 3-Buten-2-one, 4-(2,3-dihydro-1H-inden-5-yl)-

HRID 1195455Notes

Reaction equation

HRID 1195455 reaction equation
[OH-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[CH3:14][C:15]([CH3:17])=[O:16]>O>[CH2:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[CH:14][C:15](=[O:16])[CH3:17])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 1216245-Indanecarboxaldehyde

Product 1

HCID 40739273-Buten-2-one, 4-(2,3-dihydro-1H-inden-5-yl)-Yield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous solution of 10% sodium hydroxide (50-70 ml) was added dropwise over a period of 5 minutes to a suspension of indane-5-carboxaldehyde (18.50 g; 127 mmole) in acetone (50 ml) and water (50 ml). The mixture was stirred at a temperature of 65° C. for a period of 11/2 hours and then extracted with dichloromethane (200 ml). The organic extract was washed several times with water, dried over anhydrous sodium sulphate, and the solvent was removed under reduced pressure using a rotary evaporator to give 1-(5-indanyl)but-1-en-3-one (19.25 g; 81%) as a viscous oil.

Workup

  1. extractionextracted with dichloromethane (200 ml)
  2. extractionThe organic extract
  3. washwas washed several times with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-bb8f46a3df0542a6981a9802cbb25294
Source dataset
uspto-grants-1992_05
Patent number
US05110989

Reaction notes

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