Nitromethane → HCID 19974901, compound

HRID 1451492Notes

Reaction equation

HRID 1451492 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:16]([CH3:19])([O-:18])=[O:17].N12CCCN=C1CCCCC2>ClCCl>[C:10]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]([OH:9])[CH2:19][N+:16]([O-:18])=[O:17])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 13696DiphenylacetaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 19974901HCID 19974901, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fifty grams (254.78 mmol) of diphenylacetaldehyde (Aldrich) and 18.66 g (305.73 mmol) of nitromethane was dissolved in 635 mL of dichloromethane. The stirred solution was treated with 35 g of 3Å molecular sieves followed by 11.64 g (76.43 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (Aldrich) and stirred overnight at room temperature. The reaction mixture was filtered and the filtrate was treated with 700 mL of 2N aqueous HCl. The organic layer was separated and washed with saturated brine solution, dried with sodium sulfate and evaporated in vacuo. The residue was treated with 600 mL of hexane and stirred overnight whereupon crystallization occurred. After isolation there was obtained 38.22 g (58%) of 3,3-diphenyl-2-hydroxy-l-nitropropane as a pale yellow solid which was used directly in the following step.

Workup

  1. additionThe stirred solution was treated with 35 g of 3Å molecular sieves
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was treated with 700 mL of 2N aqueous HCl
  4. customThe organic layer was separated
  5. washwashed with saturated brine solution
  6. dry with materialdried with sodium sulfate
  7. customevaporated in vacuo
  8. additionThe residue was treated with 600 mL of hexane
  9. stirringstirred overnight whereupon crystallization

Sources & evidence

ORD record
ord-34f0609ed8cb40afb68acb83408ef766
Source dataset
uspto-grants-1997_02
Patent number
US05604252

Reaction notes

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