Benzyl Bromide → 4-(Phenylmethoxy)benzenebutanol

HRID 2084367Notes

Reaction equation

HRID 2084367 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[CH2:15]([O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[CH:11][CH:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 153287654-(Phenylmethoxy)benzenebutanolYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In an argon atmosphere, dry DMF (115 ml) was added to 4-(4-hydroxybutyl)phenol (9.43 g) and 65% oily sodium hydride (2.4 g), followed by stirring for 15 minutes. Next, under ice cooling and stirring, a solution of benzyl bromide (9.87 g) in dry dimethylformamide (29.5 ml) was added drop by drop, followed by stirring at the same temperature for 2 hours. After ice water and a 1 N solution of potassium hydrogen sulfate were added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, after which it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; the residue was purified by silica gel column chromatography to yield the titled compound (10.67 g) as a colorless crystalline powder.

Workup

  1. stirringNext, under ice cooling and stirring
  2. stirringby stirring at the same temperature for 2 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialafter which it was dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f31a58e6a98460ead37c6d8817eddf6
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

Loading…