Potassium Hydroxide → HCID 13066677, compound

HRID 1163990Notes

Reaction equation

HRID 1163990 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[C:16]2[O:15][C:14](=[O:17])[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[OH-:19].[K+]>CO>[OH:15][C:16]1[C:8]([O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:18])=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:13][C:14]([OH:19])=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13066702HCID 13066702, compound

Product 1

HCID 13066677HCID 13066677, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(o-Tolyloxy)-2,3-dihydrobenzofuran-2-one (2.20 g) was dissolved in a solution of potassium hydroxide (2.0 g) in methanol (30 ml), and the solution was allowed to stand at room temperature for an hour. The reaction mixture was evaporated, and the 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 oily residue was allowed to stand at room temperature and the precipitating crystals were recrystallized from a mixture of benzene and n-hexane to give prisms of 2-[2-hydroxy-3-(o-tolyloxy)phenyl]acetic acid (1.10 g). mp 116°-117° C.

Workup

  1. waitto stand at room temperature for an hour
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto stand at room temperature
  10. customthe precipitating crystals were recrystallized from a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-5137e341724944dea314abcea1dffc6e
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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