Methanol → alpha-Methylthio-alpha-(m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl)propionic acid

HRID 1733638Notes

Reaction equation

HRID 1733638 reaction equation
CO.[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH:12]=1)([CH3:10])[C:6]([O:8]C)=[O:7].[OH-].[Na+]>O>[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH:12]=1)([CH3:10])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12819455Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

Product 1

HCID 12819458alpha-Methylthio-alpha-(m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl)propionic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methanol (4 ml) and 1 ml of water were added to 1.277 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate. Furthermore, 350 mg of sodium hydroxide was added, and the mixture was heated under reflux for 2 hours. After cooling, 30 ml of water was added, and the mixture was washed twice with 10 ml of diethyl ether. To the aqueous layer was added about 6 ml of 3.5% hydrochloric acid to adjust its pH to 3. It was then extracted four times with 20 ml of diethyl ether. The organic layer was washed twice with 10 ml of water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford 1.199 g of α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionic acid as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed twice with 10 ml of diethyl ether
  5. additionTo the aqueous layer was added about 6 ml of 3.5% hydrochloric acid
  6. extractionIt was then extracted four times with 20 ml of diethyl ether
  7. washThe organic layer was washed twice with 10 ml of water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2cbf8220a12348f68e2c4ce3e2face96
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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