[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C(S)CCCC[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH:22]12[CH2:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][C:23]2=O.Cl.C[OH:32]>>[CH:22]12[CH2:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][C:23]2([C:17]1[CH:18]=[CH:19][C:20]([OH:32])=[C:15]([CH3:14])[CH:16]=1)[C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=1An appropriately sized and equipped reaction vessel was charged with o-cresol (44 g, 0.406 mol) in 10 mL MeOH and 1-dodecanethiol (1.09 mL, 0.0045 mol). The mixture was heated to 40° C. and the addition funnel was charged with 2-norbornanone (5 g, 0.045 mol) in 5 mL MeOH and o-cresol (5 g, 0.046 mol) in 5 mL MeOH. The o-cresol solution was added dropwise at 40° C. over 45 min, while introducing HCl gas under stirring. After addition, the HCl gas was bubbled for another 45 min and white precipitate was observed and color turns to light pink from dark orange. The reaction mixture was stirred for another 17 h at 40° C., GC analysis showed no starting material 2-norbornanone. The mixture was cooled to room temperature and removed MeOH using rotary evaporator and diluted with 50 mL CH2Cl2. Filter the white precipitate and washed with (3×50 mL) CH2Cl2 and dried under vacuum for 6 h gave 10.5 g (75% yield) of product as white solid with >99.9% purity by HPLC. 1HNMR, 13CNMR and MS were consistent with the structure.
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