Thionyl Chloride → 4-(2-Ethoxyethoxy)benzoyl chloride

HRID 851620Notes

Reaction equation

HRID 851620 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1)[CH3:2].S(Cl)([Cl:18])=O>O1CCOCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([Cl:18])=[O:12])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131347364-(2-Ethoxyethoxy)benzoic acid

Product 1

HCID 136684104-(2-Ethoxyethoxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7.2 g. of p-ethoxyethoxy benzoic acid, 50 ml. of dioxane and 12.2 g. of thionyl chloride was refluxed at 70° to 80° C. for 2 hours. After the reaction, excess of thionyl chloride and the solvent were recovered by a rotary evaporator to obtain a crude p-ethoxyethoxybenzoic chloride as a residue. The crude p-ethoxyethoxybenzoic acid chloride was dissolved in 70 ml. of acetone and then, a mixture of 6.6 g. of 2,3-dichloroaniline and 4.1 g. of triethylamine was added dropwise with stirring at room temperature during 30 minutes. After the addition, the mixture was stirred at the same temperature for 2 hours. After the reaction, the reaction mixture was poured into 300 ml. of 2% hydrochloric acid and the resulting precipitate was separated by a filtration. The resulting crude product was recrystallized from toluene to obtain 9.0 g. of 4-(2-ethoxyethoxy)-N-(2,3-dichlorophenyl)-benzamide. The yield was 74.4 g. The compound had a melting point of 121.2° to 122° C.

Workup

  1. additionA mixture of 7.2 g
  2. customAfter the reaction
  3. customexcess of thionyl chloride and the solvent were recovered by a rotary evaporator

Sources & evidence

ORD record
ord-3ee07b6cf5ef482f9b7b4d10177615cb
Source dataset
uspto-grants-1983_05
Patent number
US04385927

Reaction notes

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