Water → Ethyl 2,4,5-trifluorobenzoylacetate

HRID 248537Notes

Reaction equation

HRID 248537 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].O>O1CCOCC1>[F:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:3]=1[C:4](=[O:5])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 962WaterHCID 14839349HCID 14839349, compound

Product 1

HCID 2758933Ethyl 2,4,5-trifluorobenzoylacetateYield 58.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
102 °C

Procedure

A solution of 23.8 g of (2,4,5-trifluorobenzoyl)propanedioic acid, diethyl ester, 2.7 ml of water and 740 ml of p-dioxane was placed in an oil bath and stirred at 102° C. for 7 hours. The solution was then evaporated to dryness, heptane was added and the mixture refrigerated overnight. The resulting crystals were collected, washed with 10 ml of cold heptane and dried, giving 10.8 g of 2,4,5-trifluoro-β-oxobenzenepropanoic acid, ethyl ester.

Workup

  1. customThe solution was then evaporated to dryness, heptane
  2. additionwas added
  3. customthe mixture refrigerated overnight
  4. customThe resulting crystals were collected
  5. washwashed with 10 ml of cold heptane
  6. customdried

Sources & evidence

ORD record
ord-46d833d617034691ae51471592caf52c
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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