Sodium Hydroxide → HCID 14579738, compound

HRID 1607265Notes

Reaction equation

HRID 1607265 reaction equation
[C:1]([C:6]1[O:7][C:8]2[C:15]([F:16])=[CH:14][C:13]([CH2:17][CH2:18][CH3:19])=[C:12]([OH:20])[C:9]=2[C:10]=1[CH3:11])([O:3]CC)=[O:2].[OH-].[Na+]>CO>[CH3:11][C:10]1[C:9]2[C:12]([OH:20])=[C:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[C:15]([F:16])[C:8]=2[O:7][C:6]=1[C:1]([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13849543HCID 13849543, compound

Product 1

HCID 14579738HCID 14579738, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-carboethoxy-3-methyl-4-hydroxy-5-propyl-7-fluorobenzofuran (1.0 gm, 3.6 mmoles) in methanol (100 mL) was added 2N sodium hydroxide (10 mL) and the resulting solution was refluxed for a period of 4.5 hours. The reaction mixture was concentrated in vacuo. The residue was acidified with 3N hydrochloric acid and then extracted with ethylacetate. The organic phase was dried (Na2SO4), concentrated in vacuo, and 3 methyl-4 hydroxy 5 propyl 7 -fluorobenzofuran-carboxylic acid (0.79 gm; 88%) was isolated by filtering the solid after suspending in hexane.

Workup

  1. temperaturethe resulting solution was refluxed for a period of 4.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08b2b73660d847edaffed47f1ad09350
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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