Water → 1,2,2-Trichloro-3,3-dimethylcyclopropanecarboxylic acid

HRID 1197222Notes

Reaction equation

HRID 1197222 reaction equation
[Cl:1][C:2]1([C:9]([O:11]C)=[O:10])[C:4]([CH3:6])([CH3:5])[C:3]1([Cl:8])[Cl:7].S(=O)(=O)(O)O.O>C(O)=O>[Cl:1][C:2]1([C:9]([OH:11])=[O:10])[C:4]([CH3:6])([CH3:5])[C:3]1([Cl:8])[Cl:7]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13654694Methyl 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylate

Product 1

HCID 136546961,2,2-Trichloro-3,3-dimethylcyclopropanecarboxylic acidYield 36.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Methyl 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylate (10 g) was dissolved in formic acid (20 ml), and concentrated sulfuric acid (0.1 g) was added. The mixture was gently heated under reflux for 12 hours. After cooling, water (60 ml) was added to the reaction mixture. The precipitated crystals were collected by filtration, and recrystallized from hexane to give the desired 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylic acid (3.4 g) represented by the following formula. mp. 148°-150° C. ##STR25##

Workup

  1. temperatureThe mixture was gently heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-4051571866d54bfb84a7a68aec7be9c7
Source dataset
uspto-grants-1992_05
Patent number
US05117053

Reaction notes

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