Methanethiol → Methyl 2-(3-benzoylphenyl)propanoate

HRID 1277783Notes

Reaction equation

HRID 1277783 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[Na].CS.[Cl-].[NH4+]>CO.O>[C:15]([C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:14]=[CH:13][CH:12]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 878MethanethiolHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 13020172Methyl alpha-methylthio-alpha-(m-benzoylphenyl)propionate

Product 1

HCID 529083Methyl 2-(3-benzoylphenyl)propanoateYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Methyl α-methylthio-α-(m-benzoylphenyl)propionate (628 mg) was dissolved in 2 ml of anhydrous methanol, and 1.5 ml (2.34 M) of a methanol solution of sodium salt of methyl mercaptan was added. The mixture was heated under reflux for 1.5 hours. After cooling, an aqueous solution of ammonium chloride (2.0 g/10 ml) was added to stop the reaction. The reaction mixture was diluted with 10 ml of water, and then extracted with 30 ml of diethyl ether and then twice with 10 ml of diethyl ether. The extract was washed with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate and then with 5 ml of water, and dried over anhydrous sodium sulfate. The product was concentrated under reduced pressure, and the residue (377 mg) was chromatographed on a silica gel column using methylene chloride as an eluent to afford 363 mg of methyl α-(m-benzoylphenyl)propionate as a colorless oil in a yield of 68%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customthe reaction
  5. extractionextracted with 30 ml of diethyl ether
  6. washThe extract was washed with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate
  7. dry with materialwith 5 ml of water, and dried over anhydrous sodium sulfate
  8. concentrationThe product was concentrated under reduced pressure
  9. customthe residue (377 mg) was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-64624d90a52c4e8c9ed3bc5e2346e8fd
Source dataset
uspto-grants-1981_07
Patent number
US04278802

Reaction notes

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