1-(Chloromethoxy)-2-methoxyethane → HCID 10490542, compound

HRID 1417717Notes

Reaction equation

HRID 1417717 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]Cl.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 10490542HCID 10490542, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5 liter round bottom flask, fitted with a reflux condenser, dropping funnel and mechanical stirrer, was charged with p-hydroxymethylbenzyl chloride (255 g, 1.91 moles) in dichloromethane (2 liters). The flask was charged with 2-methoxyethoxymethyl chloride (300 g, 2.41 moles) and stirred at 20°-25° C. while N,N-diisopropylethylamine (500 mL, 2.86 moles) was slowly added. The reaction became exothermic and caused the dichloromethane solvent to reflux vigorously for 20 minutes. The contents were then stirred for 24 hours at room temperature. The dichloromethane extract was washed with water and brine. The remaining organics were dried over anhydrous magnesium sulfate. After removal of the solvent by rotary evaporation, the residue was passed through a plug of silica gel to provide 310 g (67% yield) of the desired product. 1H NMR spectral data were as follows: (CDCl3, 300 MHz): δ 7.35 (m, 4H), 4.80 (s, 2H), 4.62 (s, 2H), 4.58 (s, 2H), 3.72 (m, 2H), 3.58 (m, 2H), 3.4 (s, 3H).

Workup

  1. customA 5 liter round bottom flask, fitted with a reflux condenser
  2. additionwas slowly added
  3. temperatureto reflux vigorously for 20 minutes
  4. extractionThe dichloromethane extract
  5. washwas washed with water and brine
  6. dry with materialThe remaining organics were dried over anhydrous magnesium sulfate
  7. customAfter removal of the solvent
  8. customby rotary evaporation

Sources & evidence

ORD record
ord-4fb032fd42db403a9d32c39286a4dec8
Source dataset
uspto-grants-1999_03
Patent number
US05877312

Reaction notes

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