Boron trifluoride etherate → 2-(3,4-Dimethoxyphenyl)-1,3-dithiane

HRID 1415268Notes

Reaction equation

HRID 1415268 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[CH2:13]([SH:17])[CH2:14][CH2:15][SH:16].B(F)(F)F.CCOCC>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[S:17][CH2:13][CH2:14][CH2:15][S:16]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 8419Veratraldehyde

Product 1

HCID 110105922-(3,4-Dimethoxyphenyl)-1,3-dithiane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

74.7 g of 3,4-dimethoxybenzaldehyde are dissolved in 1250 ml of chloroform, treated with 50 ml of 1,3-propanedithiol and cooled at 0° C with stirring. 20 ml of boron trifluoride etherate are added and the mixture is left to stand in a refrigerator for 18 hours. The mixture is then washed three times successively with 500 ml of a 7% potassium hydroxide solution and 500 ml of a 10% sodium chloride solution. The organic extracts are combined, dried over magnesium sulphate and evaporated. The residue is recrystallized twice from ether. There are obtained 102.6 g of 2-(3,4-dimethoxyphenyl)-m-dithiane of melting point 99° - 101° C.

Workup

  1. waitthe mixture is left
  2. washThe mixture is then washed three times successively with 500 ml of a 7% potassium hydroxide solution and 500 ml of a 10% sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue is recrystallized twice from ether

Sources & evidence

ORD record
ord-ff3c07028e194c9ab8d5bdacb44fff84
Source dataset
uspto-grants-1977_01
Patent number
US04003914

Reaction notes

Loading…