Hydrochloric Acid → Cannabigerolic Acid

HRID 2201168Notes

Reaction equation

CN([CH:4]=[O:5])C.[CH3:6]/[C:7](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:8]\[CH2:9][C:10]1[C:15]([OH:16])=[CH:14][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=1[OH:22].Cl.C(Cl)(Cl)Cl.C[OH:35]>>[CH3:21][CH2:20][CH2:19][CH2:18][CH2:17][C:13]1[CH:14]=[C:15]([OH:16])[C:10]([CH2:9]/[CH:8]=[C:7](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])\[CH3:6])=[C:11]([OH:22])[C:12]=1[C:4]([OH:5])=[O:35]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 6228Dimethylformamide

HCID 5315659Cannabigerol

HCID 21584188Chloroform methanol

Product 1

HCID 6449999Cannabigerolic Acid

Conditions

Temperature: 120 °C

Procedure

6-carboxylic acid-2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol, Cannabigerolic Acid (CBGA) was prepared as follows. To a 10 mL conical flask was added 1 mL of a DMF solution of MMC. To this solution was added 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (120 mg, 0.379 mmol). The flask was heated at 120° C. for 1 hour, following which the reaction mixture was dissolved in 100 mL of chloroform:methanol (2:1) solution. The pH of this solution was adjusted with dilute HCl to pH 2.0, and then partitioned using 50 mL H2O.

Workup

custompartitioned

Sources & evidence

ORD record: ord-5eeb92887d314507a638711e1acf3b41
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359625B2

Reaction notes

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