Phenyl -Butyl Ether

Twenty-two and eight-tenths grams (0.10 mole) of n-butyl p-tolu-enesulfonate (p. 67) is added to a solution of 9.4 g. (0.1 mole) of phenol in 40 ml. of 10% aqueous sodium hydroxide solution, and the mixture is refluxed for 3 hours. After being cooled the reaction mixture is extracted with ether, and the ethereal solution is dried and distilled. There is obtained 11 g. (73%) of n-butyl phenyl ether, boiling at 72-73°/6 mm., n J 1.5049. 

Approximately 10 ml. of a solution of 57.4 ml. (0.5 mole) of silicon tetrachloride and 54.0 ml. (0.5 mole) of n-butyl bromide is added to a mixture of 12.2 g. (0.5 mole) of magnesium turnings and 300 ml. of dry ether. The reaction mixture is stirred and warmed slightly until reaction is initiated. The silicon tetrachloride-butyl bromide mixture is then added at such a rate as to promote a moderate rate of reflux. Stirring is continued for 1 hour after completion of the addition. The reflux condenser is turned downward, and the reaction mixture is 

Methyl- and ethylsilicon trichloride are prepared with a similar manner of operation in 65% and 76% yield, respectively. The methyl derivative boils at 63.5-65.6° and the ethyl at 98-100° at atmospheric pressure. 

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Potassium tert butoxide reacts with halobenzenes on heating in dimethyl sulfoxide to give ten butyl phenyl ether... 

For example /-butyl phenyl ether with aluminium chloride forms para-t-butyl phenol155. Often the de-alkylated phenol is also formed in considerable quantity. The reaction formally resembles the Fries and Claisen rearrangements. Like the Fries rearrangement the question of inter- or intramolecularity has not been settled, although may experiments based on cross-over studies156, the use of optically active ethers157 and comparison with product distribution from Friedel-Crafts alkylation of phenols158 have been carried out with this purpose in view. 

The products of the reaction are the following /-butyl-phenyl-ether (TBPE), p-/-butyl-phenol (p-TBP), o-/-butyl-phenol (o-TBP) and 2,4-di-/-butyl-phenol (2,4-DTBP). Compounds adsorbed on the external surface were recovered in methylene chloride (CH2C12) by a soxhlet treatment for 24 hours of the deactivated zeolite sample. The content of the compounds inside the zeolite (coke) was determined after dissolution, in 40 % HF at room temperature, of the catalyst recoved after 5 min, 45 min, 5h and 7.5 h extraction by CH2C12 then followed. The composition of soluble coke was investigated by analysis GC-MS. The procedure is reported in detail elsewhere [10]. 

Dialkyl peroxyphosphates 67 or monoperoxy phosphates 68 react with phenyhnagnesium bromide to afford tcrt-butyl phenyl ether in high yield together with dialkylphosphoric acid or alkylphosphoric acid in moderate yields (equation 102). 

McKenzie and Sherrington 174) found that mixtures of solid sodium or potassium phenoxide, 1-bromobutane, and polyethylene glycol) bound to cross-linked polystyrene (54) in refluxing toluene gave good yields of butyl phenyl ether (Eq. (10)). 

Exercise 14-22 Bromobenzene "reacts rapidly with potassium fert-butoxide in (CH3)2SO (methylsulfinylmethane, dimethyl sulfoxide, DMSO) to give fert-butyl phenyl ether ... 

Butyl phenyl ether. Weigh out 11.5 g (0.5 mol) of clean sodium into a dry, 1-litre round-bottomed flask provided with a double surface condenser, and... 

Bromobenzene Benzyne tert-Butyl phenyl ether... 

C10H14NO4P diethyiphosphinic acid p-nitrophenyl ester 7531-39-7 399.15 34.285 1.2 20038 C10H14O butyl phenyl ether 1126-79-0 483.15 42.268 1,2... 

C13H14 1 -methyl-7-ethylnaphthalene 2451-00-5 544.15 48.142 1,2 26101 C13H1602 propylene gtycol-sec-butyl phenyl ether. .. 482.28 42.184 2... 

Bromobenzene is converted into t-butyl phenyl ether by reaction with potassium t-butoxide in DMSO at 25° for 15 hrs. (86% yield) the reaction is much slower in t-butanol."... 

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