THE TERTIARYBUTYLBENZENES: I. ALKYLATION OF 1,4-DI-t-BUTYLBENZENE WITH t-BUTYL CHLORIDE

1955 ◽  
Vol 33 (4) ◽  
pp. 672-678 ◽  
Author(s):  
L. Ross C. Barclay ◽  
Eileen E. Betts
Keyword(s):  
Aromatic Hydrocarbon ◽  
Aluminum Chloride ◽  
Butyl Chloride ◽  
Improved Method ◽  
Alkylation Of Benzene ◽  
Amino Derivatives

The alkylation of P-di-t-butylbenzene with excess t-butyl chloride in the presence of aluminum chloride in the cold produces a new aromatic hydrocarbon, m.p. 218.5–219°. Evidence is given for the presence of an alicyclic nucleus in this hydrocarbon which analyzes for C22H34. The preparation of nitro and amino derivatives from this hydrocarbon is described. The alkylation of benzene under similar conditions yielded some 1,3,5-tri-t-butylbenzene, and an improved method of preparation of this hydrocarbon from P-di-t-butylbenzene is given.

ChemInform Abstract: EFFECT OF THE NATURE OF A SOLVENT ON THE MECHANISM OF ALKYLATION OF BENZENE WITH OLEFINS IN THE PRESENCE OF ALUMINUM CHLORIDE

1976 ◽  
Vol 7 (52) ◽  
pp. no-no
Author(s):  
M. F. POLUBENTSEVA ◽  
V. I. SORKINA ◽  
N. G. DEVYATKO ◽  
B. A. BAZHENOV ◽  
V. G. LIPOVICH
Keyword(s):  
Aluminum Chloride ◽  
Alkylation Of Benzene

REARRANGEMENT STUDIES WITH 14C: XXI. SIDE CHAIN REARRANGEMENT AND FRAGMENTATION FOLLOWING FRIEDEL–CRAFTS ALKYLATION OF BENZENE WITH β-14C-ETHYL IODIDE

1964 ◽  
Vol 42 (8) ◽  
pp. 1771-1777
Author(s):  
C. C. Lee ◽  
M. C. Hamblin ◽  
J. F. Uthe
Keyword(s):  
Reaction Time ◽  
Aluminum Chloride ◽  
Specific Activity ◽  
Ethyl Iodide ◽  
Isotopic Dilution ◽  
Side Chain ◽  
Initial Formation ◽  
Fragmentation Product ◽  
Alkylation Of Benzene ◽  
Higher Temperature

The aluminum chloride catalyzed reaction between β-14C-ethyl iodide and benzene in 1,2,4-trichlorobenzene as solvent was studied under different conditions of temperature and reaction time. Yields of ethylbenzene were estimated by isotopic dilution. Up to 20% rearranged product, α-14C-ethylbenzene, was found. The trend indicated that yield of ethylbenzene was lower and side chain rearrangement greater when the reaction mixture was heated at higher temperature for longer time. The rearrangement apparently occurred after the initial formation of β-14C-ethylbenzene. After a reaction time of 5 min at 154 °C, only 0.1–0.3% unreacted and unrearranged β-14C-ethyl iodide was recovered while the ethylbenzene obtained from the reaction showed about 2% rearrangement. When β-14C-ethylbenzene was heated with aluminum chloride in 1,2,4-trichlorobenzene for 2 or 24 h, rearrangement to α-14C-ethylbenzene was observed. In some experiments, a fragmentation product, toluene, was isolated. Its specific activity suggested that 1 mole of active ethylbenzene gave 2 moles of toluene only one of which was active. The mechanistic implications of these findings are discussed.

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