Sodium Hydroxide → HCID 15484979, compound

HRID 2305832Notes

Reaction equation

HRID 2305832 reaction equation
C([O:3][C:4](=[O:23])[C:5]([S:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([S:14][C:5]([CH3:13])([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([OH:23])=[O:3])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54165552HCID 54165552, compound

Product 1

HCID 15484979HCID 15484979, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionic acid ethyl ester (4.12 g, 12 mmol) dissolved in methanol (50 ml) and 10 N NaOH (20 ml) was added. The reaction was allowed to stir overnight at room temperature. The reaction mixture was concentrated, diluted with 1:1 hexane:diethyl ether and extracted with H2O. The water layer was cooled with ice and acidified to pH 3. The acid was then extracted with chloroform and the organic layer was dried over MgSO4, filtered and concentrated to afford of 2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionic acid as a low melting solid. Yield 580 mg, 16%; MS: 303.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with 1:1 hexane
  3. extractiondiethyl ether and extracted with H2O
  4. temperatureThe water layer was cooled with ice
  5. extractionThe acid was then extracted with chloroform
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9562a7655554d36bcb161da271f1685
Source dataset
uspto-grants-2002_08
Patent number
US06441023B1

Reaction notes

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