ChemicalBook CAS DataBase List cannabigerol

cannabigerol synthesis

5synthesis methods

Product Name:cannabigerol
CAS Number:25654-31-3
Molecular formula:C21H32O2
Molecular Weight:316.48

106-24-1
563 suppliers
$6.00/25g

500-66-3 Synthesis

500-66-3
399 suppliers
$50.00/100mg

25654-31-3
69 suppliers
$47.00/1mg

Yield:25654-31-3 80%

Reaction Conditions:

with toluene-4-sulfonic acid in chloroform at 20; for 12 h;Darkness;

Steps:

2 Example 2: Synthesis of 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (Cannabigerol (CBG)

Example 2: Synthesis of 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (Cannabigerol (CBG) (0130) CBG was synthesized following the protocol disclosed by Taura et al., (1996), The Journal of Biological Chemistry, Vol. 271, No. 21, p. 17411-17416. (0131) Geraniol (3 g, 0.0194 mol) and olivetol (2 g, 0.0111 mol) were dissolved in 400 mL of chloroform containing 80 mg of p-toluenesulfonic acid as catalyst and the reaction mixture was stirred at room temperature for 12 h in the dark. After 12 hours, the reaction mixture was washed with saturated sodium bicarbonate (400 mL) and then with H₂O (400 mL). The chloroform layer was concentrated at 40° C. under reduced pressure, and the residue obtained was chromatographed on a 2.0 cm×25 cm silica gel column using benzene (1000 mL) as the eluent to give 1.4 g (0.00442 mol) (39.9%) CBG as product. (0132) Alternatively crude CBG was purified as follows. To a 250 mL beaker was added 7.25 g crude CBG and 50 mL benzene. The flask was swirled to dissolve the CBG and 50 g silica gel was added, along with a stir bar. The solution was stirred overnight, and then poured into a 44 cm×2.75 cm column. The column was eluted with 300 mL benzene. The eluent, approximately 70 mL fractions were assayed for CBG. Fractions 1, 2, and 3 (230 mL) that contained CBG were combined and the solvent removed under pressure to give 6.464 g residue containing >80% CBG, having a purity suitable for use in the next synthetic step. (0133) In one embodiment, crude CBG was purified by mixing 7.25 g crude CBG residue with a slurry of silica gel (50 mL), in a 250 ml Beaker. This mixture was slowly agitated for 1 hour and then vacuum filtered using a fine mesh filter paper. The filter cake was washed with 250 ml benzene until a clear filtrate was obtained. The solvent from the filtrate was removed under reduced pressure to give 6.567 g of a residue having >80% CBG.

References:

US2017/283837,2017,A1 Location in patent:Paragraph 0130; 0131; 0132; 0133