Preparation of 1,1′-bi-2-naphthol

Alternative Names: 1,1′-Bi-2-naphthol; 18531-94-7;

18531-99-2; (S)-(-)-1,1′-Bi-2-naphthol; 602-09-5;
Binol;

Preparation of 1,1′-bi-2-naphthol

10 g of 2-naphthol are dissolved in an excess of ether, and 16 g (excess) of anhydrous

iron(III) chloride are gradually added to the solution in a flask fitted with a reflux
condenser. Much heat is evolved during this operation. The mixture is then refluxed
on a water bath until most of the 2-naphthol is oxidised. (To test this a small portion
of the ethereal solution is treated with an excess of dilute hydrochloric acid, and the
ether evaporated. The 1,1′-bi-2-naphthol separates out even in the warm as an oil
while 2-naphthol crystallises out on cooling.). When this is the case, the ether is
removed on a water bath, water and powdered calcium carbonate are added to the
residue, and the whole well shaken. Excess sodium hydroxide is then added, the
solution is filtered and precipitated with dilute sulfuric acid. The precipitate is washed
with boiling water or boiling ligroin, and recrystallised from benzene. Yield 4•0%
theoretical (8 g). Colourless needles from alcohol, prisms from a mixture of carbon
disulfide and alcohol; insoluble in water; slightly soluble in chloroform; soluble in
alcohol and ether; m.p. 216-218° C.

Systematic organic chemistry, by W. M. Cumming, 78, 1937.

Preparation of 4,4′-bi-1-naphthol
Alternative Names: 4,4′-Bi-1-naphthol;
[1,1′-Binaphthalene]-4,4′-diol; SBB040071; 1446-34-0;
4-(4-hydroxynaphthyl)naphthol;
4-(4-hydroxynaphthalen-1-yl)naphthalen-1-ol;
Preparation of 4,4′-bi-1-naphthol

10 g of 1•-naphthol are dissolved in the minimum quantity of boiling water (a

solution of 1•-naphthol in very dilute alcohol can also be used in the preparation),
and iron(III) chloride (ferric chloride) solution is gradually added on cooling, until the
precipitate formed is a bright reddish-violet. The latter is filtered off, and is boiled
once with water, and twice with benzene. The residue is recrystallized from alcohol.
Yield 35-40% theoretical (74 g). Shining rhombic crystals; insoluble in water; soluble
in alcohol and ether; slightly soluble in chloroform and benzene; m.p. 300° C.