Synthesis
The general procedure for the synthesis of 7-hydroxyheptanoic acid from 7-octen-1-ol was as follows: a solution of 7-octen-1-ol (1 mL, 0.88 g, 6.66 mmol, 1 eq.) in MeCN (15.8 mL, 18 mL/g) and H2O (1.8 mL, 2 mL/g) was added to a reaction vial. The reaction mixture was cooled to 0 °C and ozone was passed at a rate of 12 h at room temperature. The reaction was carried out under the protection of nitrogen at 1 atm. Subsequently, a NaHSO3 solution was prepared by dissolving Na2S2O5 (2.77 g, 14.58 mmol, 2.19 eq.) in H2O (14 mL) and this solution was slowly added to the reaction mixture, keeping the internal temperature below 35°C. After the addition was completed, the mixture was stirred for 10 minutes. EtOAc (10 mL) was added to the reaction mixture and the organic and aqueous layers were separated. The aqueous layer was further extracted with EtOAc, and all the organic layers were combined, dried with MgSO4, filtered and concentrated to give the colorless oily product 7-hydroxyheptanoic acid (0.95 g, 95% yield).
References
[1] Synlett, 2016, vol. 27, # 2, p. 245 - 248
