Ethyl Acetoacetate → 3-Chloro-but-2-enoic acid ethyl ester

HRID 19200

Reaction equation

HRID 19200 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:11]>O>[CH2:8]([O:7][C:1](=[O:6])[CH:2]=[C:3]([Cl:11])[CH3:5])[CH3:9]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 24819Phosphorus pentachloride

Product 1

HCID 2828353-Chloro-but-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of ethyl acetoacetate (150.0 g, 0.86 mol) in hexanes (200 mL) was added phosphorus pentachloride (95.0 g, 0.456 mol) at 23° C. under nitrogen and stirred for 3 h. Water (300 mL) was added to the reaction mixture while cooling in an ice-bath. The organic layer was separated, washed with an aqueous solution of 20% potassium carbonate (3×200 mL) followed by a saturated sodium chloride solution (2×100 mL), dried over sodium sulfate and concentrated in vacuo to afford 3-chloro-but-2-enoic acid ethyl ester which was purified by distillation (95.8 g, 75%): boiling range 160°-170° C.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. customThe organic layer was separated
  3. washwashed with an aqueous solution of 20% potassium carbonate (3×200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1068a9331ce242c2ba47353fc00390f7
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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