Sodium Hydroxide → HCID 14579739, compound

HRID 1607260Notes

Reaction equation

HRID 1607260 reaction equation
[C:1]([C:6]1[O:7][C:8]2[C:15]([Cl: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]([Cl:16])[C:8]=2[O:7][C:6]=1[C:1]([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13849542HCID 13849542, compound

Product 1

HCID 14579739HCID 14579739, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-carboethoxy-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (22 gm, 0.074 mole) in methanol (1.2 liter) was added 2N sodium hydroxide (120 mL) and the resulting solution was refluxed for a period of 6 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-chlorobenzofurancarboxylic acid (17 gm; 88%) was isolated by filtering the solid after suspending in hexane; m.p.: 200°-203° C.

Workup

  1. temperaturethe resulting solution was refluxed for a period of 6 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-a065006ad2f843d0908c3562aa03ba83
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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