Hexane → HCID 19744803, compound

HRID 2254401Notes

Reaction equation

HRID 2254401 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.CCCCCC>C(Cl)(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 537539293-[(Phenylmethyl)thio]benzenemethanol

Product 1

HCID 19744803HCID 19744803, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

One hundred milligrams of the alcohol obtained above was dissolved in 10 ml of chloroform, and 0.3 ml of thionyl chloride was added. The mixture was reacted at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 20 ml of water and 20 ml of ethyl ether. The ether layer was separated, and the solvent was evaporated. The residue was purified by medium-pressure liquid chromatography column: Lobar column, size A, Lichroprep Si 60F (a product of E. Merck Co.); eluting solvent: hexane] to give 55 mg (yield 51%) of 3-benzylthiobenzyl chloride as a colorless oil.

Workup

  1. customThe mixture was reacted at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 20 ml of water
  4. customThe ether layer was separated
  5. customthe solvent was evaporated
  6. customThe residue was purified by medium-pressure liquid chromatography column

Sources & evidence

ORD record
ord-e0f6b05258e447b39b0a545cf2d3f727
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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