Methanol → Methyl 4-phenylthiobenzoate

HRID 37149

Reaction equation

HRID 37149 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[S:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:21]O>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:21])=[S:12])=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178526127HCID 178526127, compound

Product 1

HCID 54459547Methyl 4-phenylthiobenzoate

Procedure

A mixture of 26.29 g of 4-phenylthiobenzoic acid, 5 ml of concentrates sulfuric acid, and 400 ml of methanol was refluxed for 10 hours while stirring. After reaction, the reaction mixture was concentrated in vacuo, and 400 ml of ethyl acetate was added to the residue, and the mixture was washed with saturated brine (200 ml×3), and dried in anhydrous magnesium sulfate, concentrated in vacuo, and methyl 4phenylthiobenzoate was obtained (27.44 g).

Workup

  1. temperaturewas refluxed for 10 hours
  2. customAfter reaction
  3. concentrationthe reaction mixture was concentrated in vacuo, and 400 ml of ethyl acetate
  4. additionwas added to the residue
  5. washthe mixture was washed with saturated brine (200 ml×3)
  6. dry with materialdried in anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-533ad2a3f35548f58abae14dec4e6bd0
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Linked notes

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