Hydroquinone → 1,4-Bis-methoxymethoxy-benzene

HRID 732299Notes

Reaction equation

HRID 732299 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-cd1254c53ba34af2a058192e881ecc8e
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

Loading…