Potassium Hydroxide → HCID 12832595, compound

HRID 1105719Notes

Reaction equation

HRID 1105719 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:5]=1[C:6]([O:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:7]>C(O)C>[Cl:3][C:4]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:5]=1[C:6]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12832594HCID 12832594, compound2×

Product 1

HCID 12832595HCID 12832595, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide, 0.8 gram (0.012 mole), was powdered and dissolved in 50 ml of ethanol. The solution was warmed to 40°-50° and 3.1 grams (0.011 mole) of (ethoxycarbonyl)methyl 2,6-dichlorobenzoate (the compound of Example IX) was added in portions during a 5-minute period. Upon completion of the addition a precipitate formed. The reaction mixture was stirred at ambient temperature for 18 hours. The potassium salt was collected by filtration, washed with ethanol, dried, placed in an Erlenmeyer flask, and stirred with 50 ml of water. To the resultant solution was added a solution of 10 ml of concentrated hydrochloric acid in 40 ml of water. The solid precipitate was collected by filtration and washed with water. The filter cake was dissolved in 100 ml of ethyl acetate and dried with sodium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to give 1.1 grams of carboxymethyl 2,6-dichlorobenzoate; mp 180°-181.5°. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. temperatureThe solution was warmed to 40°-50°
  2. additionUpon completion of the addition a precipitate
  3. customformed
  4. filtrationThe potassium salt was collected by filtration
  5. washwashed with ethanol
  6. customdried
  7. stirringstirred with 50 ml of water
  8. additionTo the resultant solution was added a solution of 10 ml of concentrated hydrochloric acid in 40 ml of water
  9. filtrationThe solid precipitate was collected by filtration
  10. washwashed with water
  11. dissolutionThe filter cake was dissolved in 100 ml of ethyl acetate
  12. dry with materialdried with sodium sulfate
  13. filtrationThe mixture was filtered
  14. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-d01d34f8d87940a896643d499c1ca395
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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