Benzaldehyde → 2-Phenyl-1,3-dithiane

HRID 604476Notes

Reaction equation

HRID 604476 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([SH:13])[CH2:10][CH2:11][SH:12].B(F)(F)F.CCOCC>C(Cl)(Cl)Cl>[C:2]1([CH:1]2[S:13][CH2:9][CH2:10][CH2:11][S:12]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8000Boron trifluoride etherateHCID 80131,3-Propanedithiol

Product 1

HCID 215472-Phenyl-1,3-dithiane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzaldehyde (15.0 g, 141 mmol) in chloroform (150 mL), propane-1,3-dithiol (16.9 g, 155 mmol) and boron trifluoride etherate (26.1 g, 183 mmol) were added. The reaction mixture was stirred at ambient temperature for 24 h, and was then poured into ice-cold aqueous sodium hydroxide (10%) and extracted with chloroform. The combined chloroform extracts were washed with water, dried over sodium sulfate, concentrated and purified by flash column chromatography using 1% ethyl acetate in hexane as eluent. Yield: 21.2 g, 77%.

Workup

  1. extractionextracted with chloroform
  2. washThe combined chloroform extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-223d3dfe4de44ec5b90c1d9e81ebb820
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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