2,5-Di-tert-butylhydroquinone → HCID 59110799, compound

HRID 1912244Notes

Reaction equation

HRID 1912244 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].ClC[CH2:21][O:22][CH2:23][CH3:24]>C1COCC1>[CH3:21][O:22][CH2:23][CH2:24][O:12][C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([O:7][CH2:24][CH2:23][O:22][CH3:21])=[CH:8][C:9]=1[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 23742,5-Di-tert-butylhydroquinoneHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydride

Product 1

HCID 59110799HCID 59110799, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Di-tert-butylhydroquinone (0.2 mmol) was dissolved in anhydrous THF (20 ml). Sodium hydride (0.6 mmol) and 2-chloroethylethylether (0.4 mmol) was then added to the solution. The reaction mixture was then stirred at room temperature overnight. After removal of the solvent, the residue was partitioned between dichloromethane and aqueous NaHCO3 (0.1M). The organic portion was separated and dried over Na2SO4. After solvent removal in vacuo, the crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1) to afford 1,4-bis(2-methoxyethoxy)-2,5-di-tert-butyl-benzene in an 81% yield. The product was characterized by 1H NMR (300 MHz, CDCl3, δ/ppm): 7.14 (s, 2H), 4.11 (t, J=4.5 Hz, 4H), 3.80 (t, J=4.5 Hz, 4H), 3.45 (s, 6H), 1.37 (s, 18H).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was partitioned between dichloromethane and aqueous NaHCO3 (0.1M)
  3. customThe organic portion was separated
  4. dry with materialdried over Na2SO4
  5. customAfter solvent removal in vacuo
  6. customthe crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1)

Sources & evidence

ORD record
ord-d9dc7b4ef8d842349f87adff41a6a4e0
Source dataset
uspto-grants-2013_12
Patent number
US08609287B2

Reaction notes

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