Ethyl Acetate → 2-Hydroxymethyl-5-pentadecylphenol

Participants

Reaction Steps

4-Pentadecylsalicylic acid (5.3 g) in dry tetrahydrofuran (60 cm3) is slowly added to stirred lithium aluminium hydride (2.5 g) in dry tetrahydrofuran (25 cm3) and the mixture then stirred and refluxed for five hours to complete the reduction. Work-up by recovery of the tetrahydrofuran, addition of a little ethyl acetate to the cooled residual material, followed by acidifiction and ethereal extraction yields the crude product which is crystallised from light petroleum (40°-60°) to give 4-pentadecylsalicyl alcohol as pale cream prisms, m.p. 94°-95°, (4.05 g).

Provenance & Evidence