Carbonic acid, bis(1,1-dimethylethyl) ester → HCID 19359302, compound

HRID 1110096Notes

Reaction equation

HRID 1110096 reaction equation
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].[C:7]([O:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:10])(C)C.[CH3:19][CH2:20][CH2:21][CH2:22]CC.[C:25]([O:28][CH2:29][CH3:30])(=[O:27])C>O1CCCC1>[C:2]([O:5][C:25]([O:28][C:29]1[CH:30]=[C:20]([CH:19]=[CH:10][C:7]=1[O:11][C:12]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:18])[CH:21]=[CH2:22])=[O:27])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 19359302HCID 19359302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

38 g (0.28 mol) 3,4-dihydroxstyrene are dissolved in 1 l of tetrahydrofuran and the solution is cooled to 5° C. With stirring and cooling, 63 g (0.56 mol) of potassium tert-butylate are added over 20 min in increments such that the temperature of the mixture remains between 5° C. The mixture is stirred for 1 h at room temperature. Then a solution of 135.3 g (0.62 mol) of di-tert-butylcarbonate in a small amount of THF is added dropwise. After stirring for c. 3 h at room temperature, analysis by thin-layer chromatography (hexane/ethyl acetate 4:1) indicates the end of the reaction. The reaction mixture is poured on to 2 kg of ice and extracted twice with diethyl ether. The organic phase is washed twice with 1N NaOH and then with water, and dried. The solvent is then removed by distillation on a rotary evaporator. The viscous residue is purified by column chromatography (silica gel, hexane/ethyl acetate 4:1).

Workup

  1. temperaturecooling
  2. customremains between 5° C
  3. stirringThe mixture is stirred for 1 h at room temperature
  4. stirringAfter stirring for c
  5. custom3 h
  6. customat room temperature
  7. customthe end of the reaction
  8. extractionextracted twice with diethyl ether
  9. washThe organic phase is washed twice with 1N NaOH
  10. dry with materialwith water, and dried
  11. customThe solvent is then removed by distillation on a rotary evaporator
  12. customThe viscous residue is purified by column chromatography (silica gel, hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-4929f84291a54afeaf4381835dfe6b1a
Source dataset
uspto-grants-1994_06
Patent number
US05324804

Reaction notes

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