Water → 1-bromo-4-propoxybenzene

HRID 493033Notes

Reaction equation

HRID 493033 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:11][CH2:12][CH2:13]Br.O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 78401-BromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 27341981-bromo-4-propoxybenzeneYield 95.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 100 ml of dimethylsulfoxide was dissolved 17.3 g (100.0 mmol) of 4-bromophenol, and an aqueous solution of sodium hydroxide (NaOH/H2O: 4.0 g/25 ml) was added thereto. The resultant mixture was stirred until dissolving homogeneously. Next was added 12.3 g (100.0 mmol) of n-propyl bromide to the resultant mixture, and the reaction was carried out at a room temperature for 24 hours. The reaction mixture was poured into an iced water, and the resultant oil was extracted with hexane. After the hexane phase was washed with water, hexane was removed from the hexane phase to give 20.5 g (95.3 mmol) of 1-bromo-4-n-propyloxybenzene.

Workup

  1. dissolutionuntil dissolving homogeneously
  2. extractionthe resultant oil was extracted with hexane
  3. washAfter the hexane phase was washed with water, hexane
  4. customwas removed from the hexane phase

Sources & evidence

ORD record
ord-1023fa67074f48fb8dc6b58ea474fde7
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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