Benzyl Bromide → 4-(Phenylmethoxy)benzenebutanol

HRID 1534300Notes

Reaction equation

HRID 1534300 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 133925134-(4-Hydroxybutyl)phenol

Product 1

HCID 153287654-(Phenylmethoxy)benzenebutanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(4-hydroxyphenyl)butanol (125 g, 0.75 mole) in acetone 0.85.8 g (1.25 mole) anhydrous potassium carbonate (285.8 g, 1.25 mole) was added, followed by 160.8 (0.94 mole) benzyl bromide. The reaction mixture was then heated at reflux for 25 hours. After cooling to room temperature, the reaction mixture was filtered and the filter cake washed with acetone. The filtrate was concentrated to dryness. The solid residue was washed twice with 500 ml hexane. After drying under high vacuum overnight, 161 g of the desired product were obtained, which was homogeneous on TLC. The 1H NMR spectrum was consistent with the assigned structure.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 25 hours
  3. filtrationthe reaction mixture was filtered
  4. washthe filter cake washed with acetone
  5. concentrationThe filtrate was concentrated to dryness
  6. washThe solid residue was washed twice with 500 ml hexane
  7. customAfter drying under high vacuum overnight

Sources & evidence

ORD record
ord-474933b94e2a4dfb814ca9e8dd132f7f
Source dataset
uspto-grants-1992_02
Patent number
US05088978

Reaction notes

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