Water → Bis(4-tert-butoxyphenyl) sulfoxide

HRID 725285Notes

Reaction equation

[Mg].[C:2]([O:6][C:7]1[CH:12]=[CH:11][C:10](Cl)=[CH:9][CH:8]=1)([CH3:5])([CH3:4])[CH3:3].[S:14](Cl)(Cl)=[O:15].[OH2:18]>C1COCC1>[C:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:14]([C:7]2[CH:12]=[CH:11][C:10]([O:18][C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:9][CH:8]=2)=[O:15])=[CH:9][CH:8]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -60 °C

Procedure

A Grignard reagent which was conventionally prepared using 24.3 g (1 mol) of magnesium, 203.2 g (1.1 mol) of 4-tert-butoxyphenyl chloride, and 280 g of THF was diluted with 500 g of THF and cooled to lower than -60° C. in a dry ice/methanol bath. Then 47.5 g (0.4 mol) of thionyl chloride diluted with 70 g of THF was added dropwise over 1 hour at less 0° C. After ripening for 1 hour in an ice bath, 36 g of water was added to decompose the excess of Grignard reagent. Separation was carried out by adding 1,000 g of methylene chloride and further 400 g of saturated ammonium chloride aqueous solution and 300 g of water. The organic layer was washed twice with 700 g of pure water. The organic layer was dried over magnesium sulfate and filtered and then evaporated. The resulting oily residue was recrystallized, isolating bis(4-tert-butoxyphenyl) sulfoxide in a yield of 60%.

Workup

additionwas added dropwise over 1 hour at less 0° C
customSeparation
additionby adding 1,000 g of methylene chloride and further 400 g of saturated ammonium chloride aqueous solution and 300 g of water
washThe organic layer was washed twice with 700 g of pure water
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customevaporated
customThe resulting oily residue was recrystallized

Sources & evidence

ORD record: ord-55789228170246aba4c3f822183ca428
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705702

Reaction notes

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