Ethyl Acetate → HCID 15634642, compound

HRID 1377215Notes

Reaction equation

HRID 1377215 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[C:11]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=O)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>O1CCCC1.O>[C:12]1([CH2:11][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:30][CH:31]=3)=[CH:21][CH:20]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 570296HCID 570296, compoundHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 15634642HCID 15634642, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a 5-liter four-necked flask equipped with a stirring device, a thermometer, a condenser and a nitrogen substituting device, 54.4 g of lithium aluminum hydride and 382.6 g of aluminum chloride were introduced slowly in 2.0 liters of tetrahydrofuran to make a mixed solution, to which 150 g of 1,1-bis(4-benzoylphenyl)methane was added at room temperature and then heated for 1 hour at 60° C. and then stirred for 4 hours with maintaining the temperature. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was cooled to room temperature and 600 milliliters of ethyl acetate was added dropwise for 30 minutes with stirring, then 500 milliliters of water was added dropwise for 30 minutes with stirring. Thereafter, the reaction solution was washed with a 6N-HCl aqueous solution, an aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and nitrobenzene by a rotary evaporator, and then subjected to a column purification with a mixed solvent of 2:1 toluene and heptane, removed off the solvent and then recrystallized from ethyl acetate, to obtain 115 g of 1,1-bis(4-(1-phenylmethyl)phenyl)methane as crystals.

Workup

  1. customIn a 5-liter four-necked flask equipped with a stirring device
  2. temperaturewith maintaining the temperature
  3. temperaturethe reaction solution was cooled to room temperature
  4. stirringwith stirring
  5. stirringwith stirring
  6. washThereafter, the reaction solution was washed with a 6N-HCl aqueous solution
  7. customan aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and nitrobenzene
  8. customby a rotary evaporator
  9. customsubjected to a column purification with a mixed solvent of 2:1 toluene and heptane
  10. customremoved off the solvent
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8e4c20b4000940d3bd1a0edc6b6e718c
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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