2-Bromopropane → 4-((4-Isopropoxyphenyl)sulfonyl)phenol

HRID 2290439Notes

Reaction equation

HRID 2290439 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:18](Br)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][CH:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1)[CH3:20]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 6626Bisphenol SHCID 11430Potassium Carbonate

Product 1

HCID 99041414-((4-Isopropoxyphenyl)sulfonyl)phenolYield 44.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

30.3 g of bis(p-hydroxyphenyl) sulfone, 18.5 g of isopropylbromide, and 22.2 g of potassium carbonate as acid-binding agent were added to 200 ml of dimethylformamide, then stirred for 4 hours at about 120° C. and dimethylformamide was distilled off under reduced pressure. When this was accomplished, chloroform was added to the residue to extract crude 4-hydroxy-4'-isopropoxydiphenylsulfone. Then this crude compound was refined by using a silica gel column chromatography and 15.7 g of 4-hydroxy-4'-isopropoxydiphenylsulfone was obtained in white microfine crystals with a melting point of 129.0°-131.0° C.

Workup

  1. distillationdimethylformamide was distilled off under reduced pressure
  2. additionchloroform was added to the residue
  3. extractionto extract crude 4-hydroxy-4'-isopropoxydiphenylsulfone

Sources & evidence

ORD record
ord-fe7c12c22a5c4d11be0cf285d8fc3446
Source dataset
uspto-grants-1986_10
Patent number
US04616239

Reaction notes

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