Ethanol → 3-Phenylpropyl 4-chloroacetoacetate

HRID 1106626Notes

Reaction equation

HRID 1106626 reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:11]1([CH2:17]CCO)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 31234BenzenepropanolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 220055463-Phenylpropyl 4-chloroacetoacetateYield 103.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 4-chloroacetoacetate (134 g, 815 mmol) and 3-phenyl-1-propanol (111 mL, 821 mmol) was heated in toluene, with azeotropic removal of ethanol, for 4 h. The solution was allowed to cool with stirring for 18 h and was then concentrated to give the title compound (214 g). Electrospray MSm /z 219 [M-Cl+H]+.

Workup

  1. temperatureto cool
  2. concentrationwas then concentrated

Sources & evidence

ORD record
ord-fe85353474a94498936b0d6800343dc1
Source dataset
uspto-grants-2000_05
Patent number
US06057332

Reaction notes

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