Cannabidiol → Tetrahydrocannabinol

HRID 426096Notes

Reaction equation

HRID 426096 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]([C@H:13]2[C@H:18]([C:19]([CH3:21])=[CH2:20])[CH2:17][CH2:16][C:15]([CH3:22])=[CH:14]2)=[C:10]([OH:12])[CH:11]=1>ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[C:9]2[C@@H:13]3[CH:14]=[C:15]([CH3:22])[CH2:16][CH2:17][C@H:18]3[C:19]([CH3:21])([CH3:20])[O:23][C:8]=2[CH:7]=1

Participants

3

Reactant 1

HCID 644019Cannabidiol

Product 1

HCID 16078Tetrahydrocannabinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cannabidiol (500 mg) in dichloromethane (8.75 mL) at 20° C., was added a solution of an organoaluminum-based Lewis acid catalyst in dichloromethane (1.0 mL) over five minutes and the reaction mixtures stirred under nitrogen and monitored by HPLC. Table 1 below shows the relative HPLC quantitation of the different product compounds in area percent at the time specified, using different organoaluminum-based Lewis acid catalysts.

Workup

  1. customover five minutes

Sources & evidence

ORD record
ord-2f7608101a864ea995147c28e9941511
Source dataset
uspto-grants-2012_01
Patent number
US08106244B2

Reaction notes

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