Potassium Hydroxide → (E)-4-(Diethoxyphosphoryl)but-2-enoic acid

HRID 333041Notes

Reaction equation

HRID 333041 reaction equation
CC[O:3][C:4](/[CH:6]=[CH:7]/[CH2:8][P:9]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:10])=[O:5].[OH-].[K+]>O>[CH2:15]([O:14][P:9]([CH2:8]/[CH:7]=[CH:6]/[C:4]([OH:5])=[O:3])([O:11][CH2:12][CH3:13])=[O:10])[CH3:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 6285301(E)-4-(Diethoxyphosphoryl)but-2-enoic acidYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of triethyl 4-phosphonocrotonate (5.53 g) in water (36 mL) was added a solution of potassium hydroxide (1.69 g) in water (36 mL) at room temperature, and the reaction solution was stirred for 3 hours. The resulting reaction solution was washed with dichloromethane, and the water layer was acidified to pH2 with concentrated hydrochloric acid and extracted with dichloromethane (550 mL). The combined organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to give 4.41 g of 4-diethylphosphonocrotonic acid as a colorless solid.

Workup

  1. customThe resulting reaction solution
  2. washwas washed with dichloromethane
  3. extractionextracted with dichloromethane (550 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-eb25510adafd499e8edcda0bb0a3d1ed
Source dataset
uspto-grants-2014_11
Patent number
US08877953B2

Reaction notes

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