4-Bromophenol → 3-(4-Bromophenoxy)propan-1-ol

HRID 2108116Notes

Reaction equation

HRID 2108116 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][CH2:14][OH:15]>CS(C)=O.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][CH2:13][CH2:14][OH:15])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 123083-Bromo-1-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 187610183-(4-Bromophenoxy)propan-1-ol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Powdered sodium hydroxide (2.2 g) was added to a solution of 4-bromophenol (3.46 g) and 3-bromopropanol (2.36 ml) in DMSO (18 ml). The mixture was stirred vigorously at 20° for 2.5 h then diluted with ethyl acetate (100 ml) and washed successively with 2N hydrochloric acid (100 ml), water (100 ml×2) and brine. Concentration of the dried organic phase yielded the title compound (5.02 g) as a pale orange oil. T.l.c. (diethyl ether) Rf 0.32.

Workup

  1. washwashed successively with 2N hydrochloric acid (100 ml), water (100 ml×2) and brine

Sources & evidence

ORD record
ord-0c5153d3f9414686aaed8628520972e6
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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