1-Butanol → HCID 178511211, compound

HRID 278525Notes

Reaction equation

HRID 278525 reaction equation
C([CH:3]=[CH2:4])=O.C([O:8][C:9](=[O:11])[CH3:10])(=O)C.C[P:13]([O:20]CCCC)(=O)OCCCC.[CH2:25]([OH:29])CCC.[C-]#[N:31].[Na+].[Cl-].[NH4+].Cl>N.C(O)(=O)C.C(O)C>[NH4+:31].[NH2:31][CH:10]([CH2:4][CH2:3][PH:13]([CH2:25][OH:29])=[O:20])[C:9]([O-:8])=[O:11]

Participants

11

Reactant 7

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 7847AcroleinHCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 16994Dibutyl methylphosphonateHCID 25517Ammonium Chloride

Product 1

HCID 178511211HCID 178511211, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 222AmmoniaSolventHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

At room temperature, 5.61 g (0.10 mol) of freshly distilled acrolein are added to 10.21 g (0.10 mol) of acetic anhydride. At 25 to 30° C., this mixture is subsequently added dropwise to 16.41 g (0.10 mol) of dibutyl methanephosphonate and 14.8 g (0.2 mol) of n-butanol. The mixture is stirred at 30° C. for 2 hours and then, at 25 to 28° C., added dropwise to a solution of 4.9 g (0.10 mol) of sodium cyanide and 10.7 g (0.20 mol) of ammonium chloride in 50 ml of ammonia (25% strength). After 2 hours at 30° C., the crude aminonitrile is added dropwise to 200 ml of hydrochloric acid (37% strength). The mixture is subsequently heated under reflux for 2 hours, while ethanol and acetic acid are distilled off. The mixture is concentrated using a rotary evaporator, a pH of approximately 9 is set using ammonia solution and the product is purified by crystallization from methanol. This gives 17.8 g (90% of theory) of 2-amino-4-(hydroxymethylphosphinyl)-butyric acid, ammonium salt.

Workup

  1. waitAfter 2 hours at 30° C.
  2. temperatureThe mixture is subsequently heated
  3. distillationare distilled off
  4. concentrationThe mixture is concentrated
  5. customa rotary evaporator
  6. customthe product is purified by crystallization from methanol

Sources & evidence

ORD record
ord-aab08cd986644b1eabb0474e17dd7f23
Source dataset
uspto-grants-2002_03
Patent number
US06359162B1

Reaction notes

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