2-(3-Methoxy-benzyl)-cyclohexanone → 7-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene

HRID 237761Notes

Reaction equation

HRID 237761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O.COC1C=C2C(C3CCCCC=3C2)=CC=1>[Pd].CO.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14]([CH:12]3[CH:7]([CH2:6]2)[CH2:8][CH2:9][CH2:10][CH2:11]3)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 148680162-(3-Methoxy-benzyl)-cyclohexanoneHCID 685259137-methoxy-2,3,4,9-tetrahydro-1H-fluorene

Product 1

HCID 685247797-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

2-(3-Methoxy-benzyl)-cyclohexanone was converted to 7-methoxy-2,3,4,9-tetrahydro-1H-fluorene in accordance with the procedure of U.S. Pat. No. 3,743,663, followed by hydrogenation (Pd/C, MeOH/EtOH, H2, 1 atm) to obtain 7-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene.

Sources & evidence

ORD record
ord-db771e7933a44babad2406ed2977bc71
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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