Water → HCID 13367668, compound

HRID 1583594Notes

Reaction equation

HRID 1583594 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[F:13][CH2:14][CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O>C(#N)C>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:10][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][F:13])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 202592671-(Chloromethyl)-4-(2-fluoroethoxy)benzene

Product 1

HCID 13367668HCID 13367668, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium hydride (0.32 g; 60% in oil) was suspended in 30 ml of dry acetonitrile, and 1.1 g of 4-methoxybenzyl alcohol was added. The mixture was stirred at 50° to 60° C. for 30 minutes. Then, 1.5 g of 4-(2-fluoroethoxy)benzyl chloride was added. The mixture was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (50 g) column chromatography (developing solvent: a 9:1 mixture of benzene and ethyl acetate) to give 1.6 g of 4-(2-fluoroethoxy)benzyl 4-methoxybenzyl ether.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure
  7. customThe resulting crude ether was purified by silica gel (50 g) column chromatography (
  8. additiona 9:1 mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-fc5ec1d0223d4612953cb98b8948e1c7
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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