5-(1,1-Dimethylheptyl)resorcinol → Nabilone

HRID 616615Notes

Reaction equation

HRID 616615 reaction equation
[CH3:1][C:2]1([CH3:10])[C@@H:5]2[C:6]([CH:8]=[CH:9][C@H:3]1[CH2:4]2)=[O:7].[CH3:11][C:12]([C:20]1[CH:21]=[C:22]([OH:27])[CH:23]=[C:24]([CH:26]=1)[OH:25])([CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH:25][C:24]1[C:23]2[C@@H:9]3[CH2:8][C:6](=[O:7])[CH2:5][CH2:4][C@H:3]3[C:2]([CH3:1])([CH3:10])[O:27][C:22]=2[CH:21]=[C:20]([C:12]([CH3:11])([CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:26]=1

Participants

5

Reactant 3

HCID 918705-(1,1-Dimethylheptyl)resorcinolHCID 6451240Aluminum(III) ChlorideHCID 10942489(+)-Apoverbenone

Product 1

HCID 5284592Nabilone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The process according to claim 7 wherein (+)-apoverbenone is reacted with about an equimolar quantity of 5-(1,1-dimethylheptyl)resorcinol in dichloromethane in the presence of about an equimolar quantity of aluminum chloride at a temperature of from about -10° C. to about 30° C. for a period of time of from about 48 to about 96 hours to form (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one.

Sources & evidence

ORD record
ord-c608d18f4a784220986674970c2a1e40
Source dataset
uspto-grants-1978_02
Patent number
US04075230

Reaction notes

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