Potassium Hydroxide → HCID 13137405, compound

HRID 1164022Notes

Reaction equation

HRID 1164022 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[O:16][C:15](=[O:18])[CH2:14][CH2:13]2.[OH-:20].[K+]>CO>[OH:16][C:17]1[C:8]([O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:19])=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][C:15]([OH:20])=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13066721HCID 13066721, compound

Product 1

HCID 13137405HCID 13137405, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-(o-tolyloxy)chroman-2-one (5.4 g) and potassium hydroxide (2 g) in methanol (50 ml) was refluxed under heating for 30 minutes. After cooling, the reaction mixture was evaporated, and the oily residue was dissolved in water, washed with diethyl ether, acidified with conc. hydrochloric acid and then extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and evaporated. The residue was recrystallized twice from a mixture of ethyl acetate and n-hexane to give 3-[2-hydroxy-3-(o-tolyloxy)phenyl]propionic acid (1.0 g). mp 106°-107° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 30 minutes
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated
  5. dissolutionthe oily residue was dissolved in water
  6. washwashed with diethyl ether
  7. extractionextracted with diethyl ether
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customThe residue was recrystallized twice from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-490199aa81df4f94a925c779042d71fa
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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