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 |
RT, room temperature; NR, no reaction.
Determined via HPLC and 1H NMR analysis.