Guaiacol → 1-Methoxy-2-(methoxymethoxy)benzene

HRID 1696699Notes

Reaction equation

HRID 1696699 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].[CH3:16][O:17][CH2:18]Cl.[Cl-].[NH4+]>CN(C=O)C.C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][O:17][CH3:18]

Participants

7

Reactant 4

HCID 460GuaiacolHCID 7864Chloromethyl Methyl EtherHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 125362771-Methoxy-2-(methoxymethoxy)benzeneYield 105.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (67.9 g, 605 mmol) was dissolved in a mixed solvent of DMF (500 mL) and THF (500 mL), then with cooling with ice, 2-methoxyphenol (68.28 g, 550 mmol) was dropwise added. This was stirred at room temperature for 2 hours, and then chloromethyl methyl ether (46 mL, 605 mmol) was added. After stirred for 5 hours at room temperature, aqueous saturated ammonium chloride solution was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, then dried with sodium sulfate, and concentrated. Purified by silica gel column chromatography, the intended compound (97.66 g, 100%) was obtained as a pale yellow oil.

Workup

  1. additionwas dropwise added
  2. stirringAfter stirred for 5 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurified by silica gel column chromatography

Sources & evidence

ORD record
ord-90220b7e318340e8835963bd19dbdb2d
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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