Acetaldehyde → HCID 17763021, compound

HRID 1379288Notes

Reaction equation

HRID 1379288 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[CH:12](=O)[CH3:13]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH:1]1([CH:7]([CH:6]2[C:12]3[C:13](=[CH:9][CH:1]=[CH:2][CH:3]=3)[CH:4]=[CH:5]2)[CH3:8])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 3

HCID 177AcetaldehydeHCID 7219IndeneHCID 14798Sodium Hydroxide

Product 1

HCID 17763021HCID 17763021, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

100.0 g (0.86 mol) of indene are dissolved in 400 ml of toluene and a solution of 86.2 g (2.2 mol) of sodium hydroxide and 19.6 g (86 mmol) of triethylbenzylammonium chloride in 86.2 ml of water (50% strength NaOH solution) is then added. The addition of 18.9 g (0.43 mol) of acetaldehyde is carried out dropwise over a period of 30 minutes. After a reaction time of 5 hours, the aqueous phase is separated off, extracted twice with 100 ml each time of diethyl ether and the combined organic phases are dried over MgSO4. The solvent is removed under reduced pressure and the crude product is purified by recrystallization from toluene/hexane. This gives 91.5 g of 1,1-bisindenylethane in 82% yield in the form of a yellow powder.

Workup

  1. customAfter a reaction time of 5 hours, the aqueous phase is separated off
  2. extractionextracted twice with 100 ml each time of diethyl ether
  3. dry with materialthe combined organic phases are dried over MgSO4
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is purified by recrystallization from toluene/hexane

Sources & evidence

ORD record
ord-8dc02d6b58f241a794e7c7d309f9ad57
Source dataset
uspto-grants-1997_09
Patent number
US05670681

Reaction notes

Loading…