Ethyl Acetoacetate → Ethyl 2-acetyl-7-chloroheptanoate

HRID 326425Notes

Reaction equation

HRID 326425 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 11746602Ethyl 2-acetyl-7-chloroheptanoateYield 102.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl acetoacetate [VI-1] (260.6 g, 2.0 mol), toluene (300 g) and 1-bromo-5-chloropentane [V-1] (311.0 g, 1.68 mol) is heated to 80°-90° C. Thereto is added anhydrous potassium carbonate (300 g), and the temperature thereof is raised to 100° C. The mixture is reacted at the same temperature for 18 hours. After completion of the reaction, the mixture is filtered, and the toluene layer is washed with water, and concentrated under reduced pressure to give crude ethyl 7-chloro-2-(1-oxo-ethyl)-heptanoate [II-1] (403.8 g, content; 68.8 %, yield; 69.1 %).

Workup

  1. temperatureis heated to 80°-90° C
  2. customThe mixture is reacted at the same temperature for 18 hours
  3. customAfter completion of the reaction
  4. filtrationthe mixture is filtered
  5. washthe toluene layer is washed with water
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-48fbe2bb42144acf90896de73871529b
Source dataset
uspto-grants-1993_12
Patent number
US05268501

Reaction notes

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