Ethyl Acetoacetate → Ethyl 2-acetyl-7-chloroheptanoate

HRID 326426Notes

Reaction equation

HRID 326426 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+]>CCCCCCC>[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 113.9%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl acetoacetate [VI-1] (218.6 g), n-heptane (200 g) and 1-bromo-5-chloropentane [V-1] (371.0 g, 2.0 mol) is heated to 90° C. Thereto is added anhydrous potassium carbonate (387 g, 2.8 mol), and the mixture is stirred with heating at 100° C. for 12 hours. The mixture is filtered with suction and the n-heptane layer is collected. The residue is washed with n-heptane (300 g), and the n-heptane layer is combined with the previous n-heptane layer, and concentrated under reduced pressure to give crude ethyl 7-chloro-2-(1-oxoethyl)heptanoate [II-1] (449.2 g), which contains 74.1 % of ethyl 7-chloro-2-(1-oxoethyl)-heptanoate and 22.1 % of 1-bromo-5-chloropentane.

Workup

  1. temperaturewith heating at 100° C. for 12 hours
  2. filtrationThe mixture is filtered with suction
  3. customthe n-heptane layer is collected
  4. washThe residue is washed with n-heptane (300 g)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0cdbd4c6cdf41f9a4149715753dda5b
Source dataset
uspto-grants-1993_12
Patent number
US05268501

Reaction notes

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