p-Toluenesulfonic acid → HCID 13924103, compound

HRID 1789244Notes

Reaction equation

HRID 1789244 reaction equation
[CH3:1][C:2]1([CH3:10])[C@@H:7]([OH:8])[CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:10])[C@@H:3]([O:9][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)[CH2:4][CH2:5][CH2:6][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 11018979(3S)-3-Hydroxy-2,2-dimethylcyclohexan-1-one

Product 1

HCID 13924103HCID 13924103, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S)-2,2-dimethyl-3-hydroxycyclohexanone (3) (5.12 g, 36.0 mmoles) and dihydropyran (5.00 g., 59.0 mmoles) were dissolved in dry methylene dichloride (90 ml). The solution was cooled in an ice bath, and p-toluenesulfonic acid (50 mg) was added. The resulting mixture was stirred at room temperature for 2 hours. After the reaction, a saturated aqueous solution of sodium hydrogencarbonate was washed with an aqueous solution of sodium chloride and dried over magnesium sulfate. The product was filtered, concentrated, and purified by distillation. Amount yielded 8.14 g (yield 99.9%).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customAfter the reaction
  3. washa saturated aqueous solution of sodium hydrogencarbonate was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered
  6. concentrationconcentrated
  7. distillationpurified by distillation
  8. customAmount yielded 8.14 g (yield 99.9%)

Sources & evidence

ORD record
ord-f96a9c2323c64a91af9d9e9bda3f3185
Source dataset
uspto-grants-1987_08
Patent number
US04687863

Reaction notes

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