Cyclohexanol → Dicyclohexyl 4,6-dimethylbenzene-1,3-disulfonate

HRID 615904Notes

Reaction equation

HRID 615904 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([CH3:23])[C:13]([S:14](Cl)(=[O:16])=[O:15])=[CH:12][C:11]([S:18](Cl)(=[O:20])=[O:19])=[C:10]([CH3:22])[CH:9]=1>N1C=CC=CC=1>[C:8]1([CH3:23])[C:13]([S:14]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])=[CH:12][C:11]([S:18]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:20])=[O:19])=[C:10]([CH3:22])[CH:9]=1

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 204669614,6-Dimethylbenzene-1,3-disulfonyl dichloride

Product 1

HCID 71331333Dicyclohexyl 4,6-dimethylbenzene-1,3-disulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Into a one liter, four-necked, round bottom flask, equipped with stirrer, condenser and thermometer, 100.0 parts of pyridine and 16.55 parts of cyclohexanol were mixed under a nitrogen atmosphere and chilled to 0° C. with an ice water bath. To this solution 25.0 parts of 1,3-xylene-4,6-disulfonyl dichloride were added in portions over thirty minutes. The solution was stirred for one hour at 0° C. and then allowed to stand for twenty-four hours at 15° C. The mixture was poured into one liter of ice water and subsequently extracted with 300 parts of methylene chloride. The organic layer was washed successively with cold 6N sulfuric acid (until the water layer was acidic to pH paper), dilute sodium bicarbonate (three times with 300 part-portions), and water (twice with 300 part-portions). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield the dicyclohexyl 1,3-xylene-4,6-disulfonate.

Workup

  1. customInto a one liter, four-necked, round bottom flask, equipped with stirrer, condenser
  2. waitto stand for twenty-four hours at 15° C
  3. extractionsubsequently extracted with 300 parts of methylene chloride
  4. washThe organic layer was washed successively with cold 6N sulfuric acid (until the water layer
  5. dry with materialIt was then dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-46adbba88779413997d3b4cf32ac0d36
Source dataset
uspto-grants-1985_02
Patent number
US04501854

Reaction notes

Loading…