Dimethyl Sulfate → HCID 21516864, compound

HRID 1758462Notes

Reaction equation

HRID 1758462 reaction equation
[OH-].[Na+].[CH:3]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH:8]1[C:4]2([C:13]([OH:15])=[O:14])[CH2:5][CH2:6][CH2:7]1.S(OC)(O[CH3:20])(=O)=O>>[CH:3]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH:8]1[C:4]2([C:13]([O:15][CH3:20])=[O:14])[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide3×HCID 574763148810-36-0

Product 1

HCID 21516864HCID 21516864, compoundYield 91%

Conditions

Temperature
50 °C

Procedure

55.0 g (0.275 mole) of a 20% aqueous sodium hydroxide solution was added dropwise to a mixture of 90.0 g (0.5 mole) of tricyclo[5.2.1.02,6 ]decane-2-carboxylic acid (mixture of endo- and exo-compounds) and 69.3 g (0.55 mole) of dimethyl sulfate over one hour under stirring at 50° C. After completion of the addition, stirring was continued at that temperature for 30 minutes. After completion of the stirring, the mixture was allowed to stand at room temperature for a while to form layers. The lower aqueous layer was taken out. The temperature was elevated again to 50° C. 55.0 g (0.275 mole) of sodium hydroxide in a 20% aqueous solution was added dropwise to the remainder over one hour under stirring at 50° C. After completion of the addition, the mixture was stirred at that temperature for 30 minutes. Then, 16.5 g (0.0825 mole) of a 20% aqueous sodium hydroxide solution was added thereto and the whole mixture was stirred at 100° C. for 45 minutes in order to decompose unreacted dimethyl sulfate. The mixture was allowed to cool and divided into layers. After the distillation, 88.3 g (yield 91.0%) of pure methyl tricyclo[5.2.1.02,6 ]decane-2-carboxylate was obtained.

Workup

  1. additionAfter completion of the addition
  2. stirringstirring
  3. customto stand at room temperature for a while
  4. customto form layers
  5. customwas elevated again to 50° C
  6. stirringunder stirring at 50° C
  7. additionAfter completion of the addition
  8. stirringthe mixture was stirred at that temperature for 30 minutes
  9. stirringthe whole mixture was stirred at 100° C. for 45 minutes in order
  10. temperatureto cool
  11. distillationAfter the distillation

Sources & evidence

ORD record
ord-1b2b4801d5b240db8f6ec46a4e3333cd
Source dataset
uspto-grants-1983_02
Patent number
US04374052

Reaction notes

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