Tert-Butylamine → Cannabichromene

HRID 1447093Notes

Reaction equation

HRID 1447093 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-Dienal2×HCID 10377Olivetol

Product 1

HCID 30219Cannabichromene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a three-necked, 2 liter round bottomed flask fitted with a condenser, a dropping funnel and a mechanical stirrer, was added 90 g. (0.5 mole) of powdered olivetol and 36.5 g. (53.2 ml., 0.5 mole) t-butylamine and the mixture dissolved in 1 liter toluene. The reaction mixture was then stirred for awhile when a brownish white gelatinous material appeared. The mixture was then heated to 50° C. and stirred constantly. To the resulting clear brown solution was added 76 g. (85.6 ml., 0.5 mole) citral dropwise. After complete addition of citral, the reaction mixture was refluxed for 9 hours, cooled to room temperature and the solvent evaporated to give 166.8 g. of crude reaction mixture.

Workup

  1. customTo a three-necked, 2 liter round bottomed flask fitted with a condenser, a dropping funnel and a mechanical stirrer
  2. additionwas added 90 g
  3. stirringstirred constantly
  4. additionTo the resulting clear brown solution was added 76 g
  5. temperaturethe reaction mixture was refluxed for 9 hours
  6. temperaturecooled to room temperature
  7. customthe solvent evaporated
  8. customto give 166.8 g
  9. customof crude reaction mixture

Sources & evidence

ORD record
ord-aa9df7f50b2a4d7e8c31d190783d39bf
Source dataset
uspto-grants-1982_02
Patent number
US04315862

Reaction notes

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