Benzaldehyde → HCID 14869924, compound

HRID 1525223Notes

Reaction equation

HRID 1525223 reaction equation
C([O-])(=O)C.[NH4+:5].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[P:14]([O-])([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]>C(O)C>[NH2:5][CH:6]([P:14](=[O:15])([O:20][CH:21]([CH3:23])[CH3:22])[O:16][CH:17]([CH3:19])[CH3:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 517165Ammonium AcetateHCID 21884945HCID 21884945, compound

Product 1

HCID 14869924HCID 14869924, compoundYield 186.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ethanol solution (1.0 L) of ammonium acetate (37.6 g, 0.5 mol) was added molecular sieves (4 A) (10.0 g), benzaldehyde (53.0 g, 0.5 mol) and diisopropyl phosphate (6-a, 83.1 g, 0.5 mol) at room temperature. The reaction mixture was stirred at 60° C. for 2 days and cooled to room temperature. The reaction mixture was concentrated and ice-water was added. Then the mixture was acidified to pH approximately 1˜2 with concentrated HCl; and the solution was washed with Et2O to remove neutral materials. The aqueous phase was then basified to pH 11 with aq NaOH, and the product was extracted with DCM. Combined layers was washed with brine, dried over Na2SO4, and concentrated to give the title compound, 6-b, (253.0 g, 41%). LC-MS: (M+H)+ 272.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionice-water was added
  4. washand the solution was washed with Et2O
  5. customto remove neutral materials
  6. extractionthe product was extracted with DCM
  7. washCombined layers was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1077131b44f240c2b0e77650a396b522
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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