Carbon Dioxide → Di-tert-butyl dicarbonate

HRID 376512Notes

Reaction equation

HRID 376512 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Na].C[C:8](C)([O-:10])C.[Na+].[C:13](=[O:15])=[O:14].[C:16]1([CH3:26])[CH:21]=CC(S(Cl)(=O)=O)=C[CH:17]=1.[OH2:27]>CN(C)CCN(C)C.C1(C)C=CC=CC=1>[C:13]([O:15][C:8]([O:10][C:16]([CH3:26])([CH3:21])[CH3:17])=[O:27])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14]

Participants

9

Reactant 6

HCID 280Carbon Dioxide3×HCID 962WaterHCID 6386tert-ButanolHCID 73974-Toluenesulfonyl chlorideHCID 5360545SodiumHCID 23676156Sodium t-butoxide

Product 1

HCID 90495Di-tert-butyl dicarbonateYield 56.4%

Reagents, catalysts & solvents 2

HCID 8037N,N,N',N'-TetramethylethylenediamineCatalystHCID 1140TolueneSolvent

Procedure

155 Grams (2.091 moles) of tert-butyl alcohol and 13.0 g (0.5652 mole) of flaky sodium were charged into a 1,000-ml glass autoclave equipped with a stirrer, thermometer, pressure gauge and gas introduction tube and were reacted with each other at 83° C. for 6 hours. After the reaction, it was difficult to stir due to the agglomeration of the formed sodium tert-butoxide. Thereafter, 200 ml of toluene was added, carbon dioxide was injected, and a reaction was carried out at 80° C. for 3 hours at the pressure of 2 kg/cm2, which consists of a partial pressure of carbon dioxide of 1 kg/cm2 and a partial pressure of air of 1 kg/cm2. After cooling, 48.51 g (0.2544 mole) of p-toluenesulfonyl chloride and 0.66 g (5.68×10-3 mole) of N,N,N',N'-tetramethylethylenediamine were added, and a reaction was carried out at 30° C. for 10 hours at the pressure of 3 kg/cm2, which consists of a partial pressure of carbon dioxide of 2 kg/cm2 and a partial pressure of air of 1 kg/cm2. After the reaction, 300 ml of water was added to the residue to dissolve the undissolved salt, the organic layer was washed twice with 200 ml of water, and the organic solvent was distilled off to give 31.31 g of di-tert-butyl dicarbonate. The yield was 56.4% based on p-toluenesulfonyl chloride.

Workup

  1. customequipped with a stirrer
  2. customthermometer, pressure gauge and gas introduction tube and were reacted with each other at 83° C. for 6 hours
  3. customAfter the reaction, it
  4. temperatureAfter cooling
  5. waita reaction was carried out at 30° C. for 10 hours at the pressure of 3 kg/cm2, which
  6. additionwas added to the residue
  7. dissolutionto dissolve the undissolved salt
  8. washthe organic layer was washed twice with 200 ml of water
  9. distillationthe organic solvent was distilled off

Sources & evidence

ORD record
ord-31687719b040424e9fcd0b29ce771f86
Source dataset
uspto-grants-2000_02
Patent number
US06020514

Reaction notes

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