4-Benzylphenol → HCID 67860114, compound

HRID 1613268Notes

Reaction equation

HRID 1613268 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:18][CH2:19][CH2:20][Cl:21]>CN(C)C=O>[CH4:3].[Cl:21][CH2:20][CH2:19][CH2:18][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 75634-BenzylphenolHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

Product 1

HCID 67860114HCID 67860114, compoundYield 164.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 2.0 g, 49 mmol) in dimethylformamide (200 mL) was added 4-benzylphenol (6.0 g, 33 mmol) portionwise. The mixture was stirred at room temperature for 2 hours, then 1-bromo-3-chloropropane (5.1 mL, 49 mmol) was added and the mixture was stirred at room temperature overnight. The reaction was quenched with methanol (10 mL) and filtered through Celite®. The filtrate was taken up in ether (300 mL), washed thrice with water (150 mL) and dried over sodium sulfate. The solution was concentrated to give 7.5 g (79%) of 4-chloropropoxyphenyl-1-phenyl-methane methane as an amber oil. 1H NMR (CDCl3): δ7.44-6.78 (m,9H), 4.01(t,2H), 3.99(s,2H), 3.55(t,2H), 1.98(m,4H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with methanol (10 mL)
  3. filtrationfiltered through Celite®
  4. washwashed thrice with water (150 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-996db55d9c4943289c5be9dcb2392c92
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

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