Water → HCID 13367630, compound

HRID 1583588Notes

Reaction equation

HRID 1583588 reaction equation
[H-].[Na+].[C:3]1([C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:14][CH2:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.O>C(#N)C>[C:3]1([C:9]([CH3:13])([CH3:12])[CH2:10][O:11][CH2:22][C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][F:14])=[CH:25][CH:24]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 219535beta,beta-DimethylbenzeneethanolHCID 202592671-(Chloromethyl)-4-(2-fluoroethoxy)benzene

Product 1

HCID 13367630HCID 13367630, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

Sodium hydride (1.4 g; 60% in oil) was added to 20 ml of dry acetonitrile, and a solution of 4.4 g of 2-phenyl-2-methylpropyl alcohol in 10 ml of acetonitrile was added dropwise at 50° C. The mixture was heated under reflux for 30 minutes, and a solution of 5.4 g of 4-(2-fluoroethoxy)benzyl chloride in 10 ml of acetonitrile was added dropwise over 10 minutes. The mixture was further heated under reflux for 1 hour. 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 (180 g) column chromatography (developing solvent: a 2:1 mixture of toluene and n-hexane) to give 6.5 g of 4-(2-fluoroethoxy)benzyl 2-phenyl-2-methylpropyl ether.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe mixture was further heated
  4. temperatureunder reflux for 1 hour
  5. extractionextracted with toluene
  6. washThe toluene layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customToluene was evaporated under reduced pressure
  9. customThe resulting crude ether was purified by silica gel (180 g) column chromatography (
  10. additiona 2:1 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-ea3e5c8e79ae4b8b89bc9679464a9db1
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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