Phenol → HCID 87219631, compound

Participants

Reaction Steps

1 g (2.93 mmol) of 4-(4-chloro-3-methyl-2-methoxyphenyl)-2-(trifluoromethyl)-hexane-1,2-diol (prepared in analogy to the sequence described in Example 110: acetylation of the corresponding phenol, Fries displacement of the acetyl group, etherification of the phenol, Wittig reaction, ene reaction, reduction of the ester to the alcohol) is reacted conventionally with SO3/pyridine complex. After three-hour stirring at room temperature the reaction mixture is poured onto a mixture of saturated NH4Cl solution and ice. It is extracted three times with methyl tert-butyl ether. The combined organic extracts are washed twice with brine and dried (Na2SO4). Following removal of the solvent on a rotary evaporator, the residue is purified by means of flash chromatography (silica gel, eluent: hexane/ethyl acetate). This gives 290 mg (29.2%) of the desired aldehyde as a mixture of the two diastereomers (in each case as a racemate).

Provenance & Evidence