Water → HCID 10728874, compound

HRID 493028Notes

Reaction equation

HRID 493028 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:18][CH2:19][CH2:20]Br.O>CS(C)=O>[CH2:18]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 78401-BromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 10728874HCID 10728874, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 75 ml of dimethylsulfoxide (DMSO) was dissolved 7.5 g (37.5 mmol) of 4-(benzyloxy)phenol, and an aqueous solution of sodium hydroxide (NaOH/H2O: 1.65 g/15 ml) was added thereto. The mixture was stirred until dissolving homogeneously. Next, 5.0 g (40.7 mmol) of n-propyl bromide was added to the mixture, and the resultant mixture was subjected to a reaction at a room temperature for 24 hours. The reaction mixture was poured into 1 L of an iced water, and a solid was formed by stirring. The resultant solid was collected by filtration, dried, and recrystallized from methanol to give 8.82 g (36.4 mmol) of 1-(n-propyloxy)-4-benzyloxybenzene.

Workup

  1. dissolutionuntil dissolving homogeneously
  2. customa solid was formed
  3. stirringby stirring
  4. filtrationThe resultant solid was collected by filtration
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-474e73ca13a94ac1b3220c5302a34fc5
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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