Formaldehyde → 5-Methoxy-2-methylindan-1-one

HRID 2228345

Reaction equation

HRID 2228345 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.C=O.[OH-].[K+].[CH3:17]CCCCC>C(O)C.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Fe].C(OC(=O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([CH3:17])[CH2:6]2

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 8058HexaneHCID 14797Potassium HydroxideHCID 787875-Methoxyindan-1-one

Product 1

HCID 122904905-Methoxy-2-methylindan-1-oneYield 44%

Reagents, catalysts & solvents 3

HCID 518773Pentacarbonyliron(0)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Methoxy indanone was treated with aqueous formaldehyde in the presence of iron pentacarbonyl and KOH in ethanol according to G. Cainelli et. al., Tetrahedron Letters 27, 2491 (1973). After chromatography (hexane:ethylacetate=7:3) over SiO2, a 44% yield of white crystals was obtained (m.p. 73-76° C.).

Sources & evidence

ORD record
ord-25fd0c8a62c34b399dc7840abb978e0e
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Linked notes

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