Sulfuric Acid → 6970-90-7

HRID 1045272Notes

Reaction equation

HRID 1045272 reaction equation
[C@@H:1]1([OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[OH:7].S(Cl)(Cl)=O.[S:13](=O)(=O)([OH:15])[OH:14].[Mn]([O-])(=O)(=O)=O.[K+].S([O-])(O)=O.[Na+]>C(Cl)Cl.C1(C)C=CC=CC=1>[O:7]1[CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]2[O:8][S:13]1(=[O:15])=[O:14]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 92886trans-1,2-CyclohexanediolHCID 516875Potassium Permanganate2×HCID 23665763Sodium Bisulfite

Product 1

HCID 4999956970-90-7Yield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Ten grams (86 mmol) of trans-1,2-cyclohexanediol (CAS No. 1460-57-7) was added to toluene, and 10 g (84 mmol) of thionyl chloride was added dropwise thereto for reaction. The resulting solution was distilled. A cyclohexanediol cyclic sulfite (trans isomer) was recovered with a yield of 90%. Next, a methylene chloride solution containing 10 g (62 mmol) of cyclohexanediol cyclic sulfite was mixed with 180 g of 10% sulfuric acid aqueous solution. The mixture was mixed with 11 g (70 mmol) of potassium permanganate in an ice bath for reaction. Thereafter, the excess amount of potassium permanganate was neutralized by sodium hydrogen sulfite. The solvent was then distilled away from the organic layer. The solid product was crystallized with diethyl ether. A purified hexahydro-1,3,2-benzodioxathiol-2,2-dioxide (trans isomer) was recovered with a yield of 24%.

Workup

  1. additionwas added dropwise
  2. customfor reaction
  3. distillationThe resulting solution was distilled
  4. customA cyclohexanediol cyclic sulfite (trans isomer) was recovered with a yield of 90%
  5. distillationThe solvent was then distilled away from the organic layer
  6. customThe solid product was crystallized with diethyl ether
  7. customA purified hexahydro-1,3,2-benzodioxathiol-2,2-dioxide (trans isomer) was recovered with a yield of 24%

Sources & evidence

ORD record
ord-f60c5240d0f7414fa73ed28a4b2a04ac
Source dataset
uspto-grants-2013_10
Patent number
US08568932B2

Reaction notes

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