Hydrogen Peroxide → 1-Fluorenemethanol

HRID 248664

Reaction equation

HRID 248664 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=CC=[CH:5][C:4]3=[CH:3][CH:2]=1.[OH:17]O.[H][H]>C(O)(=O)C.[C].[Pd].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>[OH:17][CH2:5][C:4]1[C:16]2[CH2:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]=2[CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 9154Fluoranthene3×HCID 178418361HCID 178418361, compound

Product 1

HCID 523071-Fluorenemethanol

Reagents, catalysts & solvents 3

HCID 86605258Lithium aluminum hydride aluminum chlorideCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

The process for producing 1-methyl fluorene by the reduction of 1-hydroxymethyl fluorene involves four steps when one uses fluoranthene as the starting material. The first step involves the conversion of the fluoranthene to 1-carboxylic acid fluorenone, preferably by the reaction of the fluoranthene with hydrogen peroxide in acetic acid. The resulting 1-carboxylic acid fluorenone is then reduced with hydrogen using a palladium carbon catalyst in the same manner as previously described. The resulting 1-carboxylic acid fluorene is then reduced using a lithium aluminum hydride/aluminum chloride catalyst to obtain the 1-hydroxymethyl fluorene which is then reduced with hydrogen in the presence of a palladium carbon catalyst.

Sources & evidence

ORD record
ord-b9fb1a8769b84704bdb508e85f300df6
Source dataset
uspto-grants-1993_05
Patent number
US05210352

Linked notes

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