Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate → Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-oxopropionate

HRID 1598507Notes

Reaction equation

HRID 1598507 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 18929422Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionateHCID 178418287HCID 178418287, compound

Product 1

HCID 18929426Ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-oxopropionateYield 41.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

An anhydrous methylene chloride solution of 20.0 g of ethyl 3-(2,6-dichloro-4-trifluoromethylphenyl)-3-hydroxypropionate (8) was added to a suspension of 19.6 g of pyridinium chlorochromate and 15 g of Celite in 100 ml of methylene chloride at room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with 200 ml of ether and thereafter applied to a column packed with 100 g of silica gel. Ether was used for elution, and the eluent was concentrated under reduced pressure, giving 8.3 g of the desired compound in the form of a pale brown oil (yield 41.91%).

Workup

  1. washEther was used for elution
  2. concentrationthe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9614ed74956546cc802c88ae4e2fa435
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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