Hydrochloric Acid → 2-(4-Chloro-3-methylphenoxy)acetyl chloride

HRID 2052529Notes

Reaction equation

HRID 2052529 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[O:5][CH2:6][C:7](O)=[O:8].S(Cl)([Cl:16])=O.Cl.S(=O)=O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[O:5][CH2:6][C:7]([Cl:16])=[O:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24386Thionyl Chloride2×HCID 95696Acetic acid, (4-chloro-3-methylphenoxy)-

Product 1

HCID 151109412-(4-Chloro-3-methylphenoxy)acetyl chlorideYield 84.8%

Procedure

In a 100 ml round bottom flask equipped with a reflux condenser, 27 g of 3-methyl-4-chlorophenoxyacetic acid and 32 g of thionyl chloride were charged and a small amount of zeolite was added and the mixture was refluxed until completely dissolving the reaction product. After the reaction, excess of thionyl chloride, and dissolved hydrochloric acid gas and sulfur dioxide gas were removed by a rotary evaporator and the product was distilled to obtain 25.0 g of 3-methyl-4-chlorophenoxyacetic acid chloride. The distillation was carried out at 121° to 125° C. under the pressure of 7 to 8 mmHg. The yield was 80.1%.

Workup

  1. customIn a 100 ml round bottom flask equipped with a reflux condenser
  2. temperaturethe mixture was refluxed
  3. dissolutionuntil completely dissolving the reaction product
  4. customAfter the reaction
  5. customwere removed by a rotary evaporator
  6. distillationthe product was distilled

Sources & evidence

ORD record
ord-8085a12e8a5748b3a08f082b40912c8e
Source dataset
uspto-grants-1980_01
Patent number
US04185994

Reaction notes

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