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

HRID 346250Notes

Reaction equation

HRID 346250 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-8fe499c48ee64f888aa42d6160aae429
Source dataset
uspto-grants-1991_10
Patent number
US05061731

Reaction notes

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