Phenol → HCID 20499791, compound

HRID 444360Notes

Reaction equation

HRID 444360 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].S(C1C=CC(C)=CC=1)([O:13][CH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)[CH3:17])(=O)=O>CN(C)C=O.O>[CH2:25]([O:24][C:20]1[CH:19]=[C:18]([CH:16]([CH3:17])[CH2:15][CH2:14][O:13][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 20496824HCID 20496824, compound

Product 1

HCID 20499791HCID 20499791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of phenol (4.56 g., 48.6 mmole) in dimethylformamide (40 ml.) is added under a nitrogen atmosphere to a suspension of sodium hydride (2.32 g., 48.6 mmole) of 50% (previously washed with pentane) in dimethylformamide (70 ml.) at 60° C. The reaction mixture is stirred for one hour at 60°-70° C., after which a solution of 3-(3-benzyloxyphenyl)butyl tosylate (18.9 g., 46 mmole) in dimethylformamide (80 ml.) is added. The reaction mixture is stirred at 80° C. for a half hour and is then cooled to room temperature, diluted with cold water (2500 ml.) and extracted with ether (4×400 ml.). The combined extracts are washed successively with cold 2 N hydrochloric acid (2×300 ml) and saturated sodium chloride solution (3×300 ml.) and then dried (Na2SO4). Removal of the solvent under reduced pressure affords the product as an oil. The oily residue is dissolved in benzene and filtered through silica gel (100 g.). Concentration of the filtrate under reduced pressure gives the product as an oil.

Workup

  1. washpreviously washed with pentane) in dimethylformamide (70 ml.) at 60° C
  2. stirringThe reaction mixture is stirred at 80° C. for a half hour
  3. extractionextracted with ether (4×400 ml.)
  4. washThe combined extracts are washed successively with cold 2 N hydrochloric acid (2×300 ml) and saturated sodium chloride solution (3×300 ml.)
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ba8feb54b78e4f53b8afd3e7d09049f0
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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