Dimethylformamide → Dibenzyl ether

HRID 2259754Notes

Reaction equation

HRID 2259754 reaction equation
[H-].[Na+].[CH2:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C)[CH:13]=[O:14]>>[CH2:3]([O:14][CH2:13][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydride

Product 1

HCID 7657Dibenzyl ether

Conditions

Temperature
60 °C

Procedure

This residue (non-purified) was added to a solution of 3.8 g of sodium hydride in 150 ml of dimethylformamide. The mixture was stirred at 60° C. for 30 min and the reaction mixture was cooled to room temperature. 13.7 g of benzyl chloride was added dropwise thereto and the reaction was conducted at 60° C. again for 1 h. The reaction mixture was poured into ice/water. After extraction with ethyl acetate, the extract was dried over magnesium sulfate and concentrated under reduced pressure to obtain crude benzyl ether. After purification according to silica gel column chromatography (ethylacetate/hexane=3:97), 12.0 g of the intended compound was obtained in the form of a faint yellow oil.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. waitthe reaction was conducted at 60° C. again for 1 h
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-236e454a54be4f5f942ebe147b2d0c10
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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