2,5-Di-tert-butylhydroquinone → HCID 67992966, compound

HRID 1912245Notes

Reaction equation

HRID 1912245 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+].[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl>C1COCC1>[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24][O:12][C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([O:7][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:8][C:9]=1[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 23742,5-Di-tert-butylhydroquinoneHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 67992966HCID 67992966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a manner similar to that of Example 1, by dissolving 2,5-Di-tert-butylhydroquinone (0.2 mmol) in anhydrous THF (20 ml). Sodium hydride (0.6 mmol) and 2-methoxyethoxymethyl chloride (0.4 mmol) was added to the solution. The reaction was stirred at room temperature overnight. After removal 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)methoxy]-2,5-di-tert-butyl-benzene in an 80% yield. The product was characterized by 1H NMR (300 MHz, CDCl3, δ/ppm): 7.14 (s, 2H), 5.25 (s, 4H), 3.85 (t, J=4.5 Hz, 4H), 3.61 (t, J=4.5 Hz, 4H), 3.40 (s, 6H), 1.36 (s, 18H).

Workup

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

Sources & evidence

ORD record
ord-75a74d31aabe4d389302793a78980387
Source dataset
uspto-grants-2013_12
Patent number
US08609287B2

Reaction notes

Loading…