Propylamine → Cannabichromene

HRID 1447094Notes

Reaction equation

HRID 1447094 reaction equation
[C:1]1([OH:13])[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3]([OH:4])[CH:2]=1.C(N)CC.[CH3:18][C:19](=[CH:21][CH2:22][CH2:23][C:24](=[CH:26][CH:27]=O)[CH3:25])[CH3:20]>C1(C)C=CC=CC=1>[CH3:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1[CH:5]=[C:3]([OH:4])[C:2]2[CH:27]=[CH:26][C:24]([CH2:23][CH2:22][CH:21]=[C:19]([CH3:20])[CH3:18])([CH3:25])[O:13][C:1]=2[CH:12]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 88433,7-Dimethylocta-2,6-DienalHCID 10377Olivetol

Product 1

HCID 30219Cannabichromene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction of 5 g. olivetol (27.8 mmole), 1.652 g. n-propylamine (2.3 ml., 27.8 mmole) and 4.6 ml. citral (27.8 mmole) in 55 ml. toluene was carried out in the same manner as described under Example 1. The refluxing time was 7 hours. Gas chromatographic analysis of the reaction mixture showed 61.62% CBC, 4.01% Cannabicitran and trace amount of iso-CBC.

Workup

  1. customThe reaction of 5 g

Sources & evidence

ORD record
ord-23f4ff6ceb044f328b2af0acc777d115
Source dataset
uspto-grants-1982_02
Patent number
US04315862

Reaction notes

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