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. 2020 Sep 29;83(10):2894–2901. doi: 10.1021/acs.jnatprod.0c00436

Table 3. Reaction Conditions of the Acid-Catalyzed Cyclization of CBD Using CSAa.

        reaction mixture composition (%)b
entry solvent T (°C) time (h) Δ9-THC Δ8-THC Δ8-iso-THC
1 Tol RT 48      
2 Tol RT 96 61    
3 Tol RT 120 20 28  
4 Tol 30 96 53 20  
5 Tol 40 24 48 19  
6 Tol 40 48 45 52  
7 Tol 40 72 28 72  
8 Tol 40 96 13 87  
9 Tol 50 3 37 10  
10 Tol 50 4 62 19  
11 CH2Cl2 RT 24 33 5  
12 CH2Cl2 RT 48 64 36  
13 CH2Cl2 30 24 48 52  
14 n-Hex 30 96 31 41  
15 MTBE 30 96 54 26 9
16 cyclohexane 30 96 NR NR NR
a

RT, room temperature; NR, no reaction.

b

Determined via HPLC and 1H NMR analysis.