Sulfuric Acid → Hexahydro-1,3,2-benzodioxathiole 2,2-dioxide

HRID 1045272노트

반응식

HRID 1045272 반응식
[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]

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 92886trans-1,2-CyclohexanediolHCID 516875Potassium Permanganate2회HCID 23665763Sodium Bisulfite

생성물 1

HCID 499995Hexahydro-1,3,2-benzodioxathiole 2,2-dioxide수율 90%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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%.

후처리

  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%

출처 및 근거

ORD 기록
ord-f60c5240d0f7414fa73ed28a4b2a04ac
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08568932B2

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