Dichloromethane → Methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate

HRID 647376Notes

Reaction equation

HRID 647376 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH:10]([CH3:18])[C:11]([O:16]C)=[CH:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1.Cl(O)(=O)(=O)=O.[CH2:34](Cl)Cl>>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH:10]([CH3:18])[C:11](=[O:16])[CH2:12][C:13]([O:15][CH3:34])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 538603484-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

Product 1

HCID 13576486Methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-oxopentanoate

Procedure

A mixture of the methyl ester of 4-[4-(2-chloro-4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-pentenoic acid (0.5 g), 35% aqueous perchloric acid (5 ml.) and methylene dichloride (5 ml.) is stirred at RT for 4 days. Then the solution is extracted with methylene dichloride. The combined extracts are washed, dried and evaporated. The residue is purified by prep. thin layer chromatography using 20% ethyl acetate/hexane to yield methyl 4-[4-(2-chloro-4-trifluoromethylphenoxy) phenoxy]-3- oxopentanoate.

Workup

  1. extractionThen the solution is extracted with methylene dichloride
  2. washThe combined extracts are washed
  3. customdried
  4. customevaporated
  5. customThe residue is purified by prep

Sources & evidence

ORD record
ord-9a6858dc695848bc9fc852f3753c97a1
Source dataset
uspto-grants-1983_10
Patent number
US04408076

Reaction notes

Loading…