Sodium Hydroxide → HCID 23359208, compound

HRID 232870Notes

Reaction equation

HRID 232870 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:6]=1)#[N:4]>CO>[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[CH:6]=1)#[N:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23359186Methyl 4-cyano-2-[(4-hydroxyphenoxy)methyl]benzoate

Product 1

HCID 23359208HCID 23359208, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 ml of a 3N-sodium hydroxide aqueous solution was added to 9.5 g of methyl 4-cyano-2-(4-hydroxyphenoxy)methylbenzoate obtained in Reference example 22 dissolved in 80 ml of methanol and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was removed under reduced pressure, water was added to the residue and the mixture was washed with diethyl ether and then adjusted to about pH 2 with conc. sulfuric acid. Crystals precipitated were collected by filtration and dissolved in ethyl acetate and the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was removed from the solution to obtain 5.2 g of the title compound.

Workup

  1. customobtained in Reference example 22
  2. customAfter completion of the reaction
  3. customthe solvent was removed under reduced pressure, water
  4. additionwas added to the residue
  5. washthe mixture was washed with diethyl ether
  6. customCrystals precipitated
  7. filtrationwere collected by filtration
  8. dissolutiondissolved in ethyl acetate
  9. washthe organic layer was washed with a saturated saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed from the solution

Sources & evidence

ORD record
ord-b51d0f5ed7534c8aadb14df8ff17d738
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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