Water → HCID 21434045, compound

HRID 2398798Notes

Reaction equation

HRID 2398798 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.O>CN(C)C=O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][O:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 140864-(Methylthio)phenolHCID 14797Potassium Hydroxide

Product 1

HCID 21434045HCID 21434045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.0 g (0.05 mol) of 4-(methylthio)phenol are stirred in 80 cc of absolute dimethylformamide for 30 minutes with 2.8 g (0.05 mol) of pulverized potassium hydroxide. 16.2 g (0.075 mol) of 1,4-dibromo butane are added dropwise over the course of 15 minutes and the mixture is stirred at 20° for 16 hours. After the addition of approximately 150 cc of water, the reaction mixture is extracted with ether, the extract is washed with ice-cold 1N sodium hydroxide solution and saturated sodium chloride solution, dried over sodium sulphate and evaporated. After chromatography of the residue on silica gel with hexene/ethyl acetate (99:1) and (98:2) and subsequent crystallization from petroleum ether, pure 1-(4-bromo-butyloxy)-4-(methylthio)-benzene is obtained. M.P.: 33°-34° C.

Workup

  1. extractionthe reaction mixture is extracted with ether
  2. washthe extract is washed with ice-cold 1N sodium hydroxide solution and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customAfter chromatography of the residue on silica gel with hexene/ethyl acetate (99:1) and (98:2) and subsequent crystallization from petroleum ether

Sources & evidence

ORD record
ord-7e594c64fced4dcca0c5ca65df37660a
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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