Camphor → 2,2-Diethoxy-1,7,7-trimethylbicyclo[2.2.1]heptane

HRID 406958Notes

Reaction equation

HRID 406958 reaction equation
[C:1]12(C)[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=O.[CH:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:20]([O:19][C:12]1([O:16][CH2:17][CH3:18])[CH2:7][CH:1]2[C:8]([CH3:10])([CH3:9])[C:5]1([CH3:6])[CH2:4][CH2:2]2)[CH3:21]

Participants

5

Reactant 3

HCID 2537CamphorHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformate

Product 1

HCID 681588502,2-Diethoxy-1,7,7-trimethylbicyclo[2.2.1]heptane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a flask with reflux condenser, (25 g) camphor and 50 ml absolute ethanol was taken. (36.45 g) (1.5 eq.) triethyl orthoformate and crystals of p-toluenesulfonic acid was added into the reaction mixture. The reaction mixture was heated to reflux overnight. The reaction mixture was cooled and concentrated on rotavapour and was washed with 10% potassium hydroxide solution. Extract it with dichloromethane and concentrated the organic layer on rotavapour, yellow colored liquid product was obtained. 38. g (Quantitative)

Workup

  1. temperatureTo a flask with reflux condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated on rotavapour
  6. washwas washed with 10% potassium hydroxide solution
  7. extractionExtract it with dichloromethane
  8. concentrationconcentrated the organic layer on rotavapour, yellow colored liquid product
  9. customwas obtained

Sources & evidence

ORD record
ord-dbc7cbb7aa4c47da93c472fe11353096
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Reaction notes

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