Water → HCID 21276841, compound

Participants

Reaction Steps

Lithium aluminium hydride (12 g) was suspended in dry ether (500 ml). A solution of diethyl 4-chlorohomophthalate (75 g) in ether (200 ml) was added dropwise to the above suspension over 30 minutes. The reaction mixture was heated at reflux for 2 hrs. Excess lithium aluminium hydride was decomposed carefully with water and the resulting mixture filtered through a pad of diatomaceous earth. The filtrate was partitioned between water (200 ml) and ether (800 ml). The organic layer was dried (magnesium sulphate) and evaporated in vacuo to a semi-solid which on trituation with petroleum ether (b.pt. 40°-60°) gave 2-(4-chloro-6-hydroxymethylphenyl)ethanol as a solid (45 g) m.pt. 75°-76°, characterised by its nmr spectrum.

Provenance & Evidence