Ethylene Oxide → 1-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

HRID 1588124Notes

Reaction equation

HRID 1588124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].CN(C)CCN(C)C.C([Li])CCC.[CH2:32]1[O:34][CH2:33]1.B(F)(F)F.CCOCC>O1CCCC1>[OH:34][CH2:33][CH2:32][C:5]1[C:4]([O:15][CH2:16][O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]=1[O:13][CH3:14]

Participants

7

Reactant 5

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10061046HCID 10061046, compoundHCID 178418339Butyllithium

Product 1

HCID 137145691-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

10 Grams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in 500 ml of tetrahydrofuran, then to this solution was added 7.01 ml (46.44 mM) of N,N,N',N'-tetramethylethylenediamine and the whole mixture was cooled to -78° C. in a dry ice-acetone bath. To this cooled mixture was added dropwise 29.1 ml of n-butyllithium (1.6M-hexane solution), then stirred for 30 minutes. Next, 26.4 ml (2.091M solution) of tetrahydrofuran solution of ethylene oxide and 0.5 ml of boron trifluoride-diethyl ether (BF3 ·Et2O were added to the reaction mixture. 10 Minutes after, the dry ice-acetone bath was removed from the reaction equipment, then 2 hours later, the reaction mixture was concentrated to obtain the residue and 500 ml of diethyl ether was added thereto, and washed 4 times with 200 ml of water, further washed 4 times with 200 ml of a saturated sodium chloride aqueous solution, next dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was treated by a silica gel column chromatography [diameter 6 cm×length 30 cm, eluent: ethyl acetate:n-hexane=(2:3), "Wakogel C-200"] to yield 8.5 g of 1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene. Colorless needless crystals. Melting point: 121°-123° C.

Workup

  1. custom10 Minutes after, the dry ice-acetone bath was removed from the reaction equipment
  2. concentration2 hours later, the reaction mixture was concentrated
  3. customto obtain the residue and 500 ml of diethyl ether
  4. additionwas added
  5. washwashed 4 times with 200 ml of water
  6. washfurther washed 4 times with 200 ml of a saturated sodium chloride aqueous solution
  7. dry with materialnext dried over anhydrous magnesium sulfate
  8. customAfter removal of the solvent under reduced pressure
  9. additionthe residue was treated by a silica gel column chromatography [diameter 6 cm×length 30 cm, eluent: ethyl acetate:n-hexane=(2:3), "Wakogel C-200"]

Sources & evidence

ORD record
ord-deea7595664349e7b98d71618cfc1711
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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