3 grams
of a mixture
containing equal proportions
of benzoic acid,
2-naphthol,
and 2-methoxynaphthalene
was dissolved
in 30 ml of ether, 10 ml
of water,
and
10 ml of 10% aq
sodium bicarbonate
in
a separatory funnel.

The lower layer,
containing benzoic acid,
was drained.

10 ml of 5% aq sodium hydroxide
was added
to the funnel, and
the lower layer,
containing 2-naphthol,
was drained.

5 ml of water was
added to the funnel,
and
the lower layer,
containing 2-naphthol,
was added
to the previously-drained
2-naphthol
solution.

15 ml of saturated aq sodium
chloride
was added
to the funnel,
and
the lower layer
was discarded.

The remaining
ether
layer contained
2-methoxynaphthalene.

The benzoic acid solution
was acidified
with concentrated hydrochloric acid,
and cooled
in an ice
bath.

Vacuum filtration was performed,
and
the crude product was
re-crystallized
from boiling
water.

The 2-naphthol
solution
was acidified
with concentrated hydrochloric acid,
and cooled
in an ice
bath.

Vacuum filtration
was performed,
and the crude
product
was re-crystallized from
boiling
water.

4 grams
of anhydrous
sodium sulfate
was added
to
the 2-methoxynaphthalene solution.

The solution
was
decanted
into a tared flask, and
the ether
was
evaporated.

The crude 2-methoxynaphthalene was
re-crystallized
from
methanol.

A Mel-Temp was used to
determine the
melting
points
of each
of the
recovered
substances.