Benzaldehyde → 2-Phenyl-1,3-dithiane

HRID 457278Notes

Reaction equation

HRID 457278 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>[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-dithianeYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzaldehyde (10.6 g, 100 mmol) and 1,3-propane dithiol in CH2Cl2 (150 mL) at room temperature was dropwise added BF3.Et2O (6.3 mL, 50 mmol) and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then diluted with CH2Cl2, filtered and the filtrate washed with brine, saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed under reduced pressure to afford a white solid, which was recrystallized from a 1:1 mixture of ether and hexane to afford 17.0 g (87%) of the title compound (65) as white crystalline needles. 1H NMR (CDCl3, 400 MHz): δ 1.91 (m, 1H), 2.14 (m, 1H), 2.89 (m, 2H), 3.04 (m, 2H), 5.16 (s, 1H), 7.35–7.28 (m, 3H), 7.46 (m, 2H).

Workup

  1. customat room temperature
  2. filtrationfiltered
  3. washthe filtrate washed with brine, saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto afford a white solid, which
  7. customwas recrystallized from a 1:1 mixture of ether and hexane

Sources & evidence

ORD record
ord-31c86ecb739d4072b95c94ac92f72b0c
Source dataset
uspto-grants-2007_03
Patent number
US07186855B2

Reaction notes

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