Take your phenol, dump into IPA, add some paraform and KOH - and here's your alcohol.... Of course, many assumptions are made when you put it this way; however, all looks very possible.
Patent GB893896 (http://l2.espacenet.com/dips/viewer?PN=GB893896&CY=gb&LG=en&DB=EPD)
To a flask purged with nitrogen were added 18. 3 parts by weight of 2, 6-dimethylphenol, 42 parts by weight of 14. 3% w formaldehyde in tert. butyl alcohol, and 15 parts by volume of 2. 4% w KOH in tert. butyl alcohol. The phenol/formaldehyde/KOH molar ratios were therefore 1 : 1. 33 : 1/30.
This mixture was allowed to stand overnight at 20'C under nitrogen. To it was then added enough water to make a total of 500 parts by volume, the mixture acidified with HGl, and the organic phase taken up in methylene chloride. The aqueous phase was extracted with two successive portions of methylene chloride, and the methylene chloride fractions combined. The methylene chloride was then stripped off in vacuo at 35 C and the residue extracted with isopentane to leave an insoluble powdery white residue. Additional powdery white product was precipitated from the aqueous phase by further acidification. This was washed with isopentane.
The total yield of the 3, 5-dimethyl-4- hydroxybenzyl alcohol obtained in this manner was 14. 55 parts by weight, corresponding to a conversion based on the starting phenol of 64% and a yield on the same basis of 82%. The melting point of the product was 165-169 C.
Antoncho
P.S. Dear Rhodium! This post Post 235445 (missing)
(Antoncho: "Formylations", Chemistry Discourse) is really not about formylation, but rather a hydroxymethylation - so will you please remove it from the formylation section of your site! ::)
Sorry :( ;) :)
I'll remove that from my page.
Well, actually, i didn't say 'from your page' - i said 'from the 'Formylations' section of your page' ;) :)
You could move it to the 'methylolation' section :)
There's already four nice hydroxymethylations posted only by me - this one, the other one, and two more in Post 300201 (https://www.thevespiary.org/talk/index.php?topic=11887.msg30020100#msg30020100)
(Antoncho: "3-methyl-2,5-diMeO-benzaldehyde", Novel Discourse). Considering that BzOH-BzCl-BzCN transformation is a one-pot and easy (albeit toxic) procedure and reductions of nitriles are multiple and well-documented, that might bee worth doing....... for the future generations, maybee :)
Antoncho