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

HRID 1277786
Notes
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Reaction equation

HRID 1277786 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962Water
Solvent
2×

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-9b27767a34df4042b446fab802844dd4
Source dataset
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04278802

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes