Sodium Hydroxide → E-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoic acid

HRID 978119Notes

Reaction equation

HRID 978119 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:18])=[C:9](/[CH:11]=[CH:12]/[C:13]([O:15]CC)=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:18])=[C:9](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13849545Ethyl (E)-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoate

Product 1

HCID 13849550E-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl-E-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoate (225 mg, 0.9 mmoles) (From Example 159), 2N sodium hydroxide (4 ml) and methanol (15 ml) was stirred at room temperature for 36 hours. The mixture was concentrated, acidified with 20% citric acid solution and extracted with ether. The ether solution was dried with Na2SO4, filtered and concentrated to obtain 190 mg of the title compound, m.p. 246°-248° C. (dec.).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5d4c08c195b64b72b2ba6a5bd5e0b2db
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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