Hi,

It's old, and there is no data concerning purity, but it's worth a try - one step:

US Patent 1892990

PatenteE J. 3, 1933

1,892,990

UNITED STATES PATENT OFFICE

FRANZ LINNER, OF VIENNA, AUSTRIA, ASSIGNOR, BY MESNE ASSIGNMENTS, TO BECK,

KOLLER & COMPANY, INC., OF DETROIT, MICHIGAN, A CORPORATION OF DELAWARE

PROCESS FOR THE PREPARATION OF ALKYL SUBSTITUTED AROMATIC HYDROXYL

COMPOUNDS

2. 10 parts of phenol are dissolved in 100

parts of carbon tetrachloride and the mixture

cooled to about —20° C.; 1 part of aluminum

chloride or ferric chloride or zinc chloride is

then added and propylene gas passed in until

4.9 parts of the gas are dissolved correspond-

ing to an excess of 10%. Then 0.5 parts of

normal or iso-propyl chloride is added and

the whole gradually heated during 10 hours

to a temperature of 60° C. to 70° C. in an

autoclave. Towards the conclusion of the

reaction nitrogen or carbon dioxide can be

introduced under pressure and the pressure

brought up to 2 to 3 atmospheres in order

to increase the yield. The mixture is now

decomposed with water and the solvent dis-

tilled off. It is then purified by distillation

and the reaction product collected between

225° C. and 232° C. It consists of practically

pure iso-propyl phenol giving a yield of

about 75% in the form of needles of M. Pt.

60° C.

Bill

Note for Mukkera Rajesh

Titanium Tetrachloride as a Catalyst in the Friedel-Crafts Reaction.

Part III Alkylation.

By N. M. Cullinane And D. M. Leyshon.

Journal of the Chemical Society, 1954, p. 2942-2945

Hi,

Here is a better one-step procedure – moderate yields (44-53%) but cheap: iPrOH + anisole + TiCl4 to give the demethylated product para-iPrPhOH. The mp of the benzoate of the alkali-soluble fraction is given as proof of structure; however, purity was not assessed

Bill

All materials were purified before use and precautions taken to exclude moisture.

Alkylation with Alkyl Chlorides.-The usual procedure consisted in adding the catalyst to

the other reactants in a vessel fitted with a reflux condenser, and as heat was normally evolved

cooling was applied during the addition, with continuous agitation. At the end of each alkylation the cooled product, which usually contained a little tar, was decomposed cautiously with

dilute hydrochloric acid, and the organic layer separated, washed successively with dilute

hydrochloric acid and water, and dried (CaCl2). The products formed were fractionally distilled

through a column.

Action of isoPropyl Alcohol on Anisole.-'The product collected at 200-230° was divided

into alkali-soluble and alkali-insoluble portions. The former yielded p-isopropylphenol, b. p.

228° (cf. Huston et al., J. Amer. Chem Soc., 1945, 67, 899) [benzoate, colourless plates, m. p.

71° (Tsukervanik and Nazarova, J. Gem Chew. Russia, 1937, 7, 623; Huston et al., loc. cit.)] ;

the latter consisted almost completely of p-isopropylanisole, b. p. 213" (cf. Klages, Ber., 1904,

37, 3996).

Nitration of cumene then reduction and convert the amino to phenol through diazonium salt.