Water → 4-(1,3-Dithian-2-ylidene)-4-(4-phenoxyphenyl)butyric acid

HRID 2372429Notes

Reaction equation

HRID 2372429 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][C:2]1=[C:7]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[CH2:8][CH2:9][C:10]([O:12]C)=[O:11].O>O1CCCC1.C(O)C.[OH-].[Na+]>[S:1]1[CH2:6][CH2:5][CH2:4][S:3][C:2]1=[C:7]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 2

HCID 962WaterHCID 14674064Methyl 4-(1,3-dithian-2-ylidene)-4-(4-phenoxyphenyl)-butyrate

Product 1

HCID 146740664-(1,3-Dithian-2-ylidene)-4-(4-phenoxyphenyl)butyric acidYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-(1,3-dithian-2-ylidene)-4-(4-phenoxyphenyl)-butyrate, 1.29 g, was dissolved in a solvent mixture of 30 ml of tetrahydrofuran and 30 ml of ethanol and, 10 ml of 1 N sodium hydroxide aqueous solution was added to the solution followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture. After washing with ethyl acetate, the aqueous phase was rendered acidic with conc. hydrochloric acid and extracted with ethyl acetate. After drying the ethyl acetate phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was crystallized from ether to give 1.21 g of white crystals.

Workup

  1. additionwas added to the solution
  2. washAfter washing with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying the ethyl acetate phase over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-4b39fa1ceb65491daa2194fd5748cf0a
Source dataset
uspto-grants-1992_03
Patent number
US05098928

Reaction notes

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