Olivetol → Cannabigerol

HRID 2201167Notes

Reaction equation

HRID 2201167 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10]O)/[CH3:8])[CH3:3].[C:12]1([OH:24])[CH:23]=[C:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:16]=[C:14]([OH:15])[CH:13]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:8]/[C:7](/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1])=[CH:9]\[CH2:10][C:13]1[C:12]([OH:24])=[CH:23][C:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:16][C:14]=1[OH:15]

Participants

5

Reactant 2

HCID 10377OlivetolHCID 637566Geraniol

Product 1

HCID 5315659Cannabigerol

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  1. waitAfter 12 hours
  2. washthe reaction mixture was washed with saturated sodium bicarbonate (400 mL)
  3. concentrationThe chloroform layer was concentrated at 40 C under reduced pressure
  4. customthe residue obtained
  5. customwas chromatographed on a 2.0 cm×25 cm silica gel column
  6. customto give 1.4 g (0.00442 mol)(39.9%) CBG as product

Sources & evidence

ORD record
ord-2106425fc04048d7bf390819bae276d2
Source dataset
uspto-grants-2016_06
Patent number
US09359625B2

Reaction notes

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