Benzyl Bromide → 4-(Phenylmethoxy)benzenebutanol

HRID 1745864Notes

Reaction equation

HRID 1745864 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C[O:24][CH2:23][CH2:22]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:22][CH2:23][OH:24])=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 10393TyrosolHCID 14797Potassium Hydroxide

Product 1

HCID 153287654-(Phenylmethoxy)benzenebutanol

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

In a 250 ml reaction flask 2-(4-Hydroxyphenyl)-ethanol of formula, (5) (10 g, 0.07246 mol), potassium hydroxide (6.1 g, 0.1087 mol) and catalytic amount of phase transfer catalyst tetrabutyl ammonium bromide (0.150 g) was disssolved in 65 ml of THF. Stirred it for 1.5 hr. Benzyl bromide (8.6 ml, 0.07246 mol), was added to the reaction mixture dropwise. Stirred the reaction mixture at room temperature for 4 hrs. The progress of reaction was cheked by TLC. Filtered the reaction mixture and concentrated the filtrate on rota-vapour. The crude product was recrystalised from petroleum ether to afford 4-benzyloxy-(2-phenethyl ethanol) of formula (7), 14.9 g (90%) mp 85–86° C.

Workup

  1. stirringStirred the reaction mixture at room temperature for 4 hrs
  2. customThe progress of reaction
  3. filtrationFiltered the reaction mixture
  4. concentrationconcentrated the filtrate on rota-vapour
  5. customThe crude product was recrystalised from petroleum ether

Sources & evidence

ORD record
ord-0fce68d50c9c449dbc0e3b41cf8d9bf0
Source dataset
uspto-grants-2006_03
Patent number
US07019172B2

Reaction notes

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