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Hydrochloric Acid → Methyl alpha-methylthio-alpha-(m-benzoylphenyl)propionate

HRID 1660461
Notes
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Reaction equation

HRID 1660461 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)OCC[O:18]2)[CH:12]=1)([CH3:10])[C:6]([O:8][CH3:9])=[O:7].Cl>O>[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:18])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=1)([CH3:10])[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12819455Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

Product 1

HCID 13020172Methyl alpha-methylthio-alpha-(m-benzoylphenyl)propionateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methanol (10 ml) and 1 ml of water were added to 2.52 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate, and 0.2 ml of conc. hydrochloric acid was added. The mixture was heated for 20 minutes under reflux. After cooling, 20 ml of water was added, and the mixture was extracted with 50 ml and 10 ml respectively of methylene chloride. The extract was washed twice with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was chromatographed on a column of silica gel using methylene chloride as an eluent to afford 2.10 g of methyl α-methylthio-α-(m-benzoylphenyl)-propionate as a colorless oil in a yield of 95%.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated for 20 minutes
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with 50 ml and 10 ml respectively of methylene chloride
  6. washThe extract was washed twice with 10 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-c2898493bdba45d2a2fd105c3729f149
Source dataset
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04308208

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes