p-Toluenesulfonic acid → HCID 18185253, compound

HRID 1358542Notes

Reaction equation

HRID 1358542 reaction equation
[CH3:1][C:2]1(O)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCC(C(O[C@@H]1[C@@H]2[C@@H](CC[C@H]3OC(=O)C[C@H](O)C3)[C@@H](C)C=CC2=C[C@H](C)C1)=O)(C)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 54454SimvastatinHCID 516892Sodium BicarbonateHCID 18185234HCID 18185234, compound

Product 1

HCID 18185253HCID 18185253, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.9 g (0.1 mol) of 5-methyl-2,3,4,5-tetrahydrobenzoxepin-5-ol, 300 ml of toluene and a spatula tip of para-toluenesulphonic acid are charged to a 1 litre reactor equipped with a Denan and Stark apparatus. The combined solution is brought to reflux for 2 hours, the water being removed as it is formed. The reaction mixture is then neutralized with a 5% aqueous sodium bicarbonate solution and the organic solution is washed with water. The organic phase is subsequently dried over anhydrous sodium sulphate and concentrated under reduced pressure. 16 g of the title compound are obtained, which compound is purified by distillation, B.p. (2.5 mm Hg)=80-90° C. 10 g of a colourless liquid are obtained.

Workup

  1. temperatureto reflux for 2 hours
  2. customthe water being removed as it
  3. customis formed
  4. washthe organic solution is washed with water
  5. dry with materialThe organic phase is subsequently dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efd7a8651ab04929a9d7028de49deba4
Source dataset
uspto-grants-2003_07
Patent number
US06596758B1

Reaction notes

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