Tert-Butylamine → Cannabichromene

HRID 1447092Notes

Reaction equation

HRID 1447092 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)(C)(C)C.[CH3:19][C:20](=[CH:22][CH2:23][CH2:24][C:25](=[CH:27][CH:28]=O)[CH3:26])[CH3:21]>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:28]=[CH:27][C:25]([CH2:24][CH2:23][CH:22]=[C:20]([CH3:21])[CH3:19])([CH3:26])[O:13][C:1]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 88433,7-Dimethylocta-2,6-DienalHCID 10377Olivetol

Product 1

HCID 30219Cannabichromene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a three-necked round bottomed flask (100 ml capacity), fitted with a dropping funnel and a condenser was added 5 g. olivetol (27.8 mmole) and 2.03 g. (2.96 ml., 27.8 mmole) t-butyl amine in 55 ml toluene and the mixture was heated to 50°-60° C., 4.23 g. (4.76 ml., 27.8 mmole) of citral was then added dropwise. The mixture was refluxed for 9 hours, after which time it was cooled to room temperature and the solvent evaporated to give 9.3 g. of crude reaction mixture. Gas chromatographic analysis of the reaction mixture showed 59.46% CBC (molar conversion), 5.04% cannabicitran and trace amount of iso-CBC.

Workup

  1. customTo a three-necked round bottomed flask (100 ml capacity), fitted with a dropping funnel and a condenser
  2. additionwas added 5 g
  3. temperatureThe mixture was refluxed for 9 hours
  4. customthe solvent evaporated
  5. customto give 9.3 g
  6. customof crude reaction mixture

Sources & evidence

ORD record
ord-de02050828c0415e96745021078dc4e0
Source dataset
uspto-grants-1982_02
Patent number
US04315862

Reaction notes

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