Benzyl Bromide → p-(Benzyloxy)phenethyl alcohol

HRID 1464815Notes

Reaction equation

HRID 1464815 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10393TyrosolHCID 23665647Potassium tert-butoxide

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-hydroxyphenethyl alcohol (33 g, 0.24 mol) in dry dimethylformamide (200 ml), cooled to 0° C., was added potassium tert-butoxide (29 g, 0.26 mol) by portions. After 10 minutes, benzyl bromide (41 g, 0.28 mol) was added slowly. The reaction mixture was stirred for 15 minutes at 0° C., then for 3 hours at room temperature and was quenched with water (200 ml). The precipitate was collected, dried and recrystallized from isopropyl ether/hexanes (34 g).

Workup

  1. waitfor 3 hours at room temperature
  2. customwas quenched with water (200 ml)
  3. customThe precipitate was collected
  4. customdried
  5. customrecrystallized from isopropyl ether/hexanes (34 g)

Sources & evidence

ORD record
ord-22221002ad8b4b41905de3519618714f
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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