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2,3-Naphthalenedicarboxaldehyde (10.0 g) in dry tetrahydrofuran (100ml) was added to phenylmagnesium bromide [derived from bromobenzene (53 g) and magnesium (8 g)] in dry tetrahydrofuran (500 ml) over 1 hr. and the solution was refluxed for a further 3 hr. On cooling, water (500 ml) was added and the ethereal layer was decanted. The aqueous slurry was washed with ether (4 × 500 ml) and the combined ethereal extracts were dried (magnesium sulphate) and evaporated to dryness. The residue was purified by chromatography on silica gel and recrystallised from dichloromethane/petroleum ether (b.p. 40°-60°) to yield two isomers of 2,3-bis(1-phenyl-1-hydroxymethyl)naphthalene (III) (8.0 g. m.p. 145° and 3.0 g, m.p. 164°).

1. temperatureand the solution was refluxed for a further 3 hr
2. temperatureOn cooling
3. customthe ethereal layer was decanted
4. washThe aqueous slurry was washed with ether (4 × 500 ml)
5. dry with materialthe combined ethereal extracts were dried (magnesium sulphate)
6. customevaporated to dryness
7. customThe residue was purified by chromatography on silica gel
8. customrecrystallised from dichloromethane/petroleum ether (b.p. 40°-60°)