Trimethyl orthoformate → 1,1-Dimethoxy-1,2,3,4-tetrahydronaphthalene

HRID 406964Notes

Reaction equation

HRID 406964 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8]C=2)[CH2:4][CH2:3][CH2:2]1.[CH:12](OC)([O:15][CH3:16])[O:13][CH3:14].F[P-](F)(F)(F)(F)F.[H+].C([O-])(O)=O.[Na+]>CO>[CH3:14][O:13][C:12]1([O:15][CH3:16])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 107241-TetraloneHCID 516892Sodium BicarbonateHCID 16211447Hexafluorophosphoric acid

Product 1

HCID 145462871,1-Dimethoxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask, (10 g) 1-tetralone in 20 ml methanol, 15 ml (2 equiv.) trimethyl orthoformate was taken and the mixture was stirred at room temperature. 0.2 ml hexafluoro phosphoric acid (catalytic amount) was added and the mixture was refluxed for 5.5 hrs. The mixture was then cooled at 25-30° C. After completion of reaction dilute the reaction mass by adding 10% NaHCO3 solution and extract with ethyl acetate. The organic layer was washed with NaHCO3 solution. Dry it by adding sodium sulfate, concentrate it on rotavapour to give dark brown colored oily product.

Workup

  1. temperaturethe mixture was refluxed for 5.5 hrs
  2. temperatureThe mixture was then cooled at 25-30° C
  3. customAfter completion of reaction
  4. additiondilute the reaction mass
  5. extractionextract with ethyl acetate
  6. washThe organic layer was washed with NaHCO3 solution
  7. customDry it
  8. additionby adding sodium sulfate
  9. concentrationconcentrate it on rotavapour
  10. customto give dark brown colored oily product

Sources & evidence

ORD record
ord-c6f9b51ada7c4d0f970232173a37ddb9
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Reaction notes

Loading…