Hydroquinone → 1,4-Bis-methoxymethoxy-benzene

HRID 1176815Notes

Reaction equation

HRID 1176815 reaction equation
[H-].[Na+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].[CH3:11][O:12][CH2:13]Cl.[CH2:15]([O:17][CH2:18]C)C>CN(C=O)C>[CH3:11][O:12][CH2:13][O:4][C:3]1[CH:10]=[CH:9][C:7]([O:8][CH2:15][O:17][CH3:18])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 3283Diethyl EtherHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 5426431,4-Bis-methoxymethoxy-benzeneYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Stir a suspension of sodium hydride (60% in mineral oil, 3.81 g, 95.45 mmol) in anhydrous DMF (50 mL) under nitrogen atmosphere at 0° C. and add a solution of hydroquinone (5.00 g, 45.45 mmol) in anhydrous DMF (50 mL) dropwise. Add to this suspension methoxymethyl chloride (7.2 mL, 95.45 mmol) dropwise with additional gas evolution noted. Allow the reaction to warm to ambient temperature and stir for one hour. Quench the reaction with water and add diethyl ether. Wash the organic layer with 1N sodium hydroxide and brine. Dry the organic layer over sodium sulfate, concentrate in vacuo, and flash chromatograph with 20% ethyl acetate/hexane to yield 1,4-bis-methoxymethoxy-benzene 6 (5.64 g, 63%) as a clear oil. 1H NMR (CDCl3): 6.97 (s, 4H), 5.11 (s, 4H), 3.47 (s, 6H).

Workup

  1. customthe reaction
  2. stirringstir for one hour
  3. customQuench
  4. customthe reaction with water
  5. washWash the organic layer with 1N sodium hydroxide and brine
  6. dry with materialDry the organic layer over sodium sulfate
  7. concentrationconcentrate in vacuo, and flash chromatograph with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d7b2366b98e840548c7008a06fcb4cb9
Source dataset
uspto-grants-2010_11
Patent number
US07842822B2

Reaction notes

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