p-Toluenesulfonic acid → 1,1-Dimethoxycycloheptane

HRID 406965Notes

Reaction equation

HRID 406965 reaction equation
[C:1]1(=O)[CH2:7][CH2:6]C[CH2:4][CH2:3][CH2:2]1.[CH:9](OC)([O:12][CH3:13])[O:10][CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:11][O:10][C:9]1([O:12][CH3:13])[CH2:4][CH2:3][CH2:2][CH2:1][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 10400Cycloheptanone

Product 1

HCID 128928771,1-Dimethoxycycloheptane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

To a flask with reflux condenser (5 g) cycloheptanone, and 10 ml methanol was taken. (10 ml) (2.0 eq.) trimethyl orthoformate and several crystals of p-toluenesulfonic acid were added in to the reaction mixture and the mixture was stirred at 25-30° C. to about 1.5 hrs. Color of the reaction mixture became pale yellow. Reaction was monitored by TLC. Then remove the methanol on rotavapour. Water was added in to the reaction mixture and extract with ethyl acetate. Organic layer was washed with 5% sodium bicarbonate solution then water and brine solution. Concentrate it on rotavapor yellow colored oily product obtained.

Workup

  1. customReaction
  2. customThen remove the methanol on rotavapour
  3. additionWater was added in to the reaction mixture
  4. extractionextract with ethyl acetate
  5. washOrganic layer was washed with 5% sodium bicarbonate solution
  6. concentrationConcentrate it on rotavapor yellow colored oily product
  7. customobtained

Sources & evidence

ORD record
ord-bd7164368be74073b7ad743e61e7e025
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Reaction notes

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