HCID 523520, compound → Methyl-beta-(m-methoxyphenyl)-beta-methoxy-propionate

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[OH:6].[CH3:16]I.[H-].[Na+]>>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[O:6][CH3:16]

Participants

Reactant 2

HCID 523520HCID 523520, compound

HCID 23686416Methyl iodide sodium hydride

Product 1

HCID 20376249Methyl-beta-(m-methoxyphenyl)-beta-methoxy-propionate

Procedure

Methylβ-(m-methoxyphenyl)-β-hydroxy-propionate was reacted with methyl iodide/sodium hydride to give methyl-β-(m-methoxyphenyl)-β-methoxy-propionate, which was then reduced with LiAlH4 in dry ether to give 3-(m-methoxyphenyl)-3-methoxy-propanol. This latter product was converted into 3-(m-methoxyphenyl)-3-methoxy-propanal by oxidation with pyridinium chlorochromate in dry dichloromethane.

Sources & evidence

ORD record: ord-1a9b05a06d1141f8960a7121f061329e
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04186142

Reaction notes

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