Bromhydrol → Nabilone

HRID 972941Notes

Reaction equation

HRID 972941 reaction equation
[OH:1][C:2]1[C:11]2[C@H:10]3[CH2:12][C:13](=[O:16])[CH2:14][CH2:15][C@H:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[OH:1][C:2]1[C:11]2[C@@H:10]3[CH2:12][C:13](=[O:16])[CH2:14][CH2:15][C@H:9]3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=[C:4]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 86735145cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

Product 1

HCID 5284592Nabilone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

To a solution of 1.0 g. of dl-cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one in 40 ml. of dichloromethane was added in one portion 1.0 g. of aluminum bromide. The reaction mixture was stirred for five hours at 24° C., and then was washed with 1N hydrochloric acid solution and with water. The reaction mixture was dried and the solvent was removed by evaporation under reduced pressure, thus providing dl-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Workup

  1. washwas washed with 1N hydrochloric acid solution and with water
  2. customThe reaction mixture was dried
  3. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fe71dd87d364406481a65cee04caf5a3
Source dataset
uspto-grants-1977_10
Patent number
US04054582

Reaction notes

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