Ethanol → 2-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenoxy]acetic acid

HRID 922321Notes

Reaction equation

HRID 922321 reaction equation
CCO.C1COCC1.[CH3:9][O:10]/[N:11]=[C:12](/[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[CH2:13][O:14][C:15]1[CH:35]=[CH:34][C:18]([CH2:19][O:20][C:21]2[CH:33]=[CH:32][C:24]([O:25][CH2:26][C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.[OH-].[Na+]>O>[CH3:9][O:10]/[N:11]=[C:12](/[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[CH2:13][O:14][C:15]1[CH:35]=[CH:34][C:18]([CH2:19][O:20][C:21]2[CH:33]=[CH:32][C:24]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 88581771HCID 88581771, compound

Product 1

HCID 885830402-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenoxy]acetic acidYield 49.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged 3 mL of ethanol and 3 mL of THF. To the stirred solvent was added ethyl {4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenoxy}acetate (0.13 g, 1.289 mmol) and NaOH was added followed by water (1 mL) at 0° C. Then it was stirred at RT for 5 h. After completion of the reaction (reaction monitored by TLC), reaction mixture was evaporated completely and the crude was washed with ether, and diluted with water and then neutralized with 1N HCl, then extracted with ethyl acetate, organic layer was washed with water and brine, dried over sodium sulphate. The organic layer was evaporated on rotavapor to give the product (0.06 g Yield: 49.5%). Purity: 97.98%

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionwas added
  3. customAfter completion of the reaction (reaction monitored by TLC), reaction mixture
  4. customwas evaporated completely
  5. washthe crude was washed with ether
  6. additiondiluted with water
  7. extractionextracted with ethyl acetate, organic layer
  8. washwas washed with water and brine
  9. dry with materialdried over sodium sulphate
  10. customThe organic layer was evaporated on rotavapor
  11. customto give the product (0.06 g Yield: 49.5%)

Sources & evidence

ORD record
ord-d23dccefd54c42f9803a85f2b1921e79
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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