4-Isopropylphenol → HCID 20066036, compound

HRID 359074Notes

Reaction equation

HRID 359074 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[K+]>CS(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 74654-IsopropylphenolHCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 20066036HCID 20066036, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-isopropylphenol (16.3 g), 4-chloronitrobenzene (15.8 g), dimethylsulfoxide (150 ml) and potassium hydroxide (5.6 g) was stirred at 90° C. for 48 hours. The reaction solution was poured into ice-water (500 ml), and extracted with ethyl acetate (250 ml), washed (3 times) with water, and d ried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give 4-(4-isopropylphenoxy)nitrobenzene (29.6 g). Further, it was dissolved in ethanol (300 ml), and thereto was added 5 % palladium/carbon (2.9 g) and the mixture was subjected to catalytic reduction at room temperature for 18 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 4-(4-isopropylphenoxy)aniline (24.6 g).

Workup

  1. extractionextracted with ethyl acetate (250 ml)
  2. washwashed (3 times) with water
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-21e82db5631749e38828ea66c4b19e91
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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