Hydrochloric Acid → 1-[3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl]-ethanone

HRID 418936Notes

Reaction equation

HRID 418936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:29](Cl)(=[O:31])[CH3:30].Cl>O.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:16]([C:29](=[O:31])[CH3:30])=[CH:15][C:14]2[CH2:13][CH:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:11]3[CH:6]([C:5]=2[CH:4]=1)[CH2:7][CH2:8][CH2:9][CH2:10]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 666521086-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

Product 1

HCID 666521131-[3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl]-ethanoneYield 55.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Combine 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (0.13 g, 0.4 mmol) and methylene chloride (6 ml). Cool to −5° C. and add aluminum chloride (0.11, 0.81 mmol) followed by acetyl chloride (0.032 g, 0.4 mmol). After 2 hours, add ice, water and 1N HCl. Filter precipitate and rinse filtrate with sodium bicarbonate solution solution followed by brine. Remove solvent in vacuo, and chromatograph on silica gel with 17% ethyl acetate/hexanes to yield the titled compound (0.081 g, 55%). 1H NMR (CDCl3). MS m/z 365, (M+1).

Workup

  1. filtrationFilter precipitate
  2. washrinse filtrate with sodium bicarbonate solution solution

Sources & evidence

ORD record
ord-adf699f8cd1f417f914b15e246f88058
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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