Ethyl Acetoacetate → Ethyl 2-chloroacetoacetate

HRID 977045Notes

Reaction equation

HRID 977045 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].S(Cl)([Cl:13])(=O)=O>C(Cl)Cl>[Cl:13][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 24648Sulfuryl chloride

Product 1

HCID 11858Ethyl 2-chloroacetoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

32.5 g (0.25 mol) of ethyl acetoacetate are dissolved in 64 ml of methylene chloride. 33.74 g (0.25 mol) of sulfuryl chloride are added dropwise to this solution, and the mixture is then (when the evolution of gas is complete) heated at a gentle boil for one hour. After the methylene chloride has been removed by distillation, the residue is distilled at 86°-92° C./12 mmHg. 38.8 g of substance are obtained, 1H NMR: --CH3 1.31 ppm (t, 3H), --CH2 --(ester) 4.28 ppm (q, 2H), --CH3 (acetyl) 2.38 ppm (s, 3H), --CHCl--4.76 ppm (s, 1H).

Workup

  1. temperatureheated at a gentle boil for one hour
  2. customAfter the methylene chloride has been removed by distillation
  3. distillationthe residue is distilled at 86°-92° C./12 mmHg
  4. custom38.8 g of substance are obtained

Sources & evidence

ORD record
ord-bf88a87c46844b97b201a3209fffb366
Source dataset
uspto-grants-1997_03
Patent number
US05614351

Reaction notes

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