Thiophenol → HCID 12522571, compound

HRID 437108Notes

Reaction equation

HRID 437108 reaction equation
[OH-].[K+].[CH3:3][S:4]([CH2:6]Cl)=[O:5].[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([S:14][CH2:6][S:4]([CH3:3])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 151872Methane, chloro(methylsulfinyl)-

Product 1

HCID 12522571HCID 12522571, compoundYield 87.6%

Conditions

Temperature
60 °C

Procedure

Potassium hydroxide (460 mg) was added in an atmosphere of nitrogen to a mixture of 560 mg of chloromethyl methyl sulfoxide and 616 mg of thiophenol, and then the mixture was heated at 60° C. for 13.5 hours. With addition of 3 ml. of water, the mixture was extracted with chloroform. The extract was dried using anhydrous sodium sulfate, and then subjected to column-chromatography [silica gel, chloroform-ethyl acetate (9:1 )] to yield 812 mg of methyl phenylthiomethyl sulfoxide having a boiling point of 148° C./0.5 mmHg and an nD25 of 1.6053 as a colorless liquid in a yield of 87.3%.

Workup

  1. additionWith addition of 3 ml
  2. extractionof water, the mixture was extracted with chloroform
  3. customThe extract was dried

Sources & evidence

ORD record
ord-8319681a216d471c9c6dd0b6c65f7633
Source dataset
uspto-grants-1977_06
Patent number
US04029712

Reaction notes

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