Acetic Acid → HCID 86615476, compound

HRID 2079579Notes

Reaction equation

HRID 2079579 reaction equation
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2].C([O-])(=O)C.[NH4+].C(O)(=O)C.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:6]([O:5][P:4]([C:3]([C:1]#[N:2])=[CH:27][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:11])[O:8][CH2:9][CH3:10])[CH3:7]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 75676Diethyl (cyanomethyl)phosphonateHCID 517165Ammonium Acetate

Product 1

HCID 86615476HCID 86615476, compound

Procedure

To a stirred solution of diethyl cyanomethylphosphonate (32.6 g, 184 mmol), ammonium acetate (6.0 g, 78 mmol), acetic acid (6 mL) in toluene (120 mL) was added cyclohexanecarboxyaldehyde (21 g, 174 mmol). The reaction mixture was stirred at room temperature for two days and then heated at 100° C. for 3 hours. After cooling, the reaction mixture washed with saturated sodium bicarbonate solution three times, with brine one time and then dried over magnesium sulfate. The reaction mixture was filtered and concentrated to yield a residue. The residue was purified by Kugelrohr distillation to yield [1-cyano-2-(cyclohexyl)-vinyl]-phosphonic acid diethyl ester as a light brown oil.

Workup

  1. temperatureheated at 100° C. for 3 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture washed with saturated sodium bicarbonate solution three times, with brine one time
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated
  7. customto yield a residue
  8. distillationThe residue was purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-a77bf12418d7444a98bebb932c165df5
Source dataset
uspto-grants-2011_04
Patent number
US07932261B2

Reaction notes

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