Ethanol → HCID 23332058, compound

HRID 1706408Notes

Reaction equation

HRID 1706408 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([OH:18])[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(O)C.[OH-].[K+]>O1CCOCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([OH:18])[C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 23332066HCID 23332066, compound

Product 1

HCID 23332058HCID 23332058, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
27 °C

Procedure

A mixture of ethyl 4-(1-pyrrolyl)phenylglycolate (0.49 g, 0.002 mole), ethanol (10 ml), dioxane (1.2 ml) and 2 M aqueous KOH (1.5 ml) was stirred at 27° C. for 3 hrs., and then evaporated to dryness. The residue was dissolved in H2O. The solution was acidified with acetic acid and extracted with ethyl acetate (3×15 ml). The combined extracts after washing with H2O and drying (MgSO4), evaporation and recrystallization of the residue from H2O gave 0.19 g (44%) of 4-(1-pyrrolyl)phenylglycolic acid, m.p. 168°-168.5° C.

Workup

  1. custom, and then evaporated to dryness
  2. dissolutionThe residue was dissolved in H2O
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. washThe combined extracts after washing with H2O
  5. customdrying
  6. custom(MgSO4), evaporation and recrystallization of the residue from H2O

Sources & evidence

ORD record
ord-83633863c4fd478cb9a6eb4cdd4849e6
Source dataset
uspto-grants-1980_06
Patent number
US04207329

Reaction notes

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