Water → HCID 14349147, compound

HRID 414830Notes

Reaction equation

HRID 414830 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:16]=[CH:17][CH:18]=1.[OH-].[Na+].O>CS(C)=O>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=[C:3]1[CH2:2][O:12][C:13]1[CH:14]=[C:15]([CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 117900843-(1-Hydroxyhexyl)phenolHCID 123263162-(Bromomethyl)-1-benzofuran

Product 1

HCID 14349147HCID 14349147, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromomethylbenzofuran (5 g, 0.024 mol) and 1-(3-hydroxyphenyl)-1-hexanol (4.7 g,0.024 mol) were dissolved in DMSO (75 ml). To this clear, homogeneous solution was added an aqueous solution of sodium hydroxide (12.5 ml, 2N solution; 0.025 mol NaOH). Immediately after the sodium hydroxide solution was added, the reaction mixture became warm (45°-50° C.). This clear, homogeneous solution was stirred at room temperature for 6 hours, and then poured into water (300 ml). The organics were extracted thoroughly with ethyl acetate (3×50 ml), and the combined organic extract was washed with water, 1N sodium hydroxide solution (to remove excess phenol), water, 0.1N hydrochloric acid solution, water and finally brine. After drying over anhydrous magnesium sulfate, all volatiles were removed from the ethyl acetate extract to leave a clear liquid (7.2 g) which was chromatographed on silica gel using 10% ethyl acetate in hexanes as eluent to obtain the pure compound as a clear, colorless liquid (4.4 g, 56%).

Workup

  1. temperaturethe reaction mixture became warm (45°-50° C.)
  2. extractionThe organics were extracted thoroughly with ethyl acetate (3×50 ml)
  3. extractionthe combined organic extract
  4. washwas washed with water, 1N sodium hydroxide solution (to remove excess phenol), water, 0.1N hydrochloric acid solution, water and finally brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customall volatiles were removed from the ethyl acetate
  7. extractionextract

Sources & evidence

ORD record
ord-124bca6c741d4e26958f6401a6340c65
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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