Methanol → HCID 19879357, compound

HRID 1885604Notes

Reaction equation

HRID 1885604 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][C:25](C)(C)C)=[O:23])[C:12]([O:14]C(C)(C)C)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 19879355HCID 19879355, compound

Product 1

HCID 19879357HCID 19879357, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of di-tert-butyl 2-(3,4-dichlorophenylthiomethyl)adipate (550 mg) in benzene (7 ml) was added p-toluenesulfonic acid (40 mg), and the mixture was refluxed for 45 minutes. After the reaction mixture was cooled to room temperature, methanol (7 ml) was added, and the solution was stirred at 40° C. for 2.5 hours. The reaction mixture was concentrated in vacuo, and the resulting residue was purified by flash column chromatography on silica by eluting with chloroform/methanol (10:1) to give 340 mg of 3-(3,4-dichlorophenylthio)-2-(3-methoxycarbonylpropyl)propionic acid as an oil.

Workup

  1. temperaturethe mixture was refluxed for 45 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting residue was purified by flash column chromatography on silica
  4. washby eluting with chloroform/methanol (10:1)

Sources & evidence

ORD record
ord-363b83549cff4ca98cc01a39d240c47f
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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