Sodium Hydroxide → HCID 15484979, compound

HRID 1595560Notes

Reaction equation

HRID 1595560 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-42be655ee41c4a8bb6821e0d82dbc9c9
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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