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

HRID 1660462Notes

Reaction equation

HRID 1660462 reaction equation
[CH3:1][S:2][C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](OC)([O:22]C)[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].COCCOC.O.Cl>C(Cl)Cl>[CH3:1][S:2][C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 80711,2-DimethoxyethaneHCID 12819452Methyl alpha-methylthio-alpha-(m-(alpha,alpha-dimethoxybenzyl)phenyl)propionate

Product 1

HCID 13020172Methyl alpha-methylthio-alpha-(m-benzoylphenyl)propionateYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 978 mg of methyl α-methylthio-α-[m-(α,α-dimethoxybenzyl)phenyl]propionate were added 2 ml of 1,2-dimethoxyethane and 0.5 ml of water, and 0.2 ml of conc. hydrochloric acid was further added. The mixture was stirred at room temperature for 15 hours. The reaction solution was diluted with 50 ml of methylene chloride, and dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure to afford 874 mg of methyl α-methylthio-α-(m-benzoylphenyl)propionate. The product was found to be substantially pure by its NMR and GLC.

Workup

  1. additionwas further added
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe drying agent was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a680645ff4054e579766539d1b07a2e4
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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