4-Toluenesulfonyl chloride → HCID 14088496, compound

Participants

Reaction Steps

This compound was prepared after the method of Moulines et al, Synthesis, (1981), 550. 18 g 2-ethylhexa e-1, 3-diol (Aldrich Chemical Co.) was dissolved in dry THF (350 ml) and the solution was chilled to -3° C. (ice-salt bath). n-Butyllithium solution (1.6M in hexane, 94 ml, 0.15 mol) was added dropwise with stirring over 45 minutes (temperature 5°±5° C.). Stirring was continued for a further 1 hour at room temperature, then p-toluenesulphonyl chloride (28.6 g, 0.15 mol) in dry THF (75 ml) was added dropwise over 45 minutes with cooling in an ice-bath. After a further period of stirring of 1 hour a second portion of n-butyl lithium (94 ml) was added over 30 minutes at 5°-10° C. (ice-bath cooling), and the mixture was stirred overnight at room temperature. Finally, the mixture was heated at 60°-65° C. for 2.5 hours (thick white suspension forms), prior to concentration in vacuo, addition of water (750 ml) and continuous extraction with ether for 4 hours. After removal of the ether the resulting pale yellow oil was distilled to give 5.25 g (33%) of (CXXIII), bp 70.4°-71.8° C./100 mbar.

Provenance & Evidence