Methanol → HCID 12917671, compound

HRID 1733612Notes

Reaction equation

HRID 1733612 reaction equation
CO.[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=1)([CH3:10])[C:6]([O:8]C)=[O:7].[OH-].[K+]>O>[CH3:3][S:4][C:5]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:15][CH:16]=1)([CH3:10])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 12917661HCID 12917661, compound

Product 1

HCID 12917671HCID 12917671, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

Water (2 ml) and 4 ml of methanol were added to 420 mg of methyl α-methylthio-α-(p-isobutylphenyl)propionate. Then, 280 mg (85% content) of potassium hydroxide was added, and the mixture was stirred at 60° C. for 2.5 hours. The reaction mixture, initially heterogeneous, became uniform. Water (30 ml) was added, and the mixture was extracted with 10 ml of methylene chloride. The aqueous layer was acidified with conc. hydrochloric acid to a pH of 1, and extracted three times with 20 ml of diethyl ether. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the diethyl ether. Thus, 394 mg of crude α-methylthio-α-(p-isobutylphenyl)propionic acid was obtained as an oil in a yield of 99%. The oil soon crystallized, and recrystallization from water-methanol afforded colorless crystals having a melting point of 89° to 92° C.

Workup

  1. extractionthe mixture was extracted with 10 ml of methylene chloride
  2. extractionextracted three times with 20 ml of diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the diethyl ether

Sources & evidence

ORD record
ord-85efae49837c4e30a7e2331860030510
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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