Catechol → HCID 10655488, compound

HRID 1740119Notes

Reaction equation

HRID 1740119 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[Na].Cl[CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13]>CO.C[O-].[Na+]>[OH:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 289CatecholHCID 28659Methyl 2-chloropropionateHCID 5360545Sodium

Product 1

HCID 10655488HCID 10655488, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Catechol (55 g) was dissolved in a methanol solution of sodium methoxide prepared from metallic sodium (11.5 g). Methyl 2-chloropropionate (62 g) was added thereto and refluxed. Extraction with ether and purification on a silica gel column afforded 15 g of methyl 2-(2-hydroxyphenoxy)propionate. This product and 3,4-dichlorobenzylcyanide were dissolved in an ethanol solution of sodium ethoxide prepared from metallic sodium (7 g), and the mixture was refluxed with heat for 3 hours. Extraction with ether and purification on a silica gel column afforded 3 g of 2-(3,4-dichlorophenyl)-4-(2-hydroxyphenyl)-3-oxopentanonitrile. This compound (1 g), 2,3-dichloro-5-trifluoromethylpyridine (0.6 g), and potassium carbonate (0.4 g) were dissolved in dimethylformamide, and the mixture was stirred for 2 hours at 120° C. Extraction with ether and purification on a silica gel column afforded 0.6 g of 4-[2-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-(3,4-dichlorophenyl)-3-oxopentanonitrile (Compound 18).

Workup

  1. temperaturerefluxed
  2. extractionExtraction
  3. customwith ether and purification on a silica gel column

Sources & evidence

ORD record
ord-868cbbe531504aa795ee633921950684
Source dataset
uspto-grants-1999_10
Patent number
US05968977

Reaction notes

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