Acetonitrile → 3-Methoxy-5-(3-methoxy-propoxy)-benzaldehyde

HRID 1698357Notes

Reaction equation

HRID 1698357 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:15][OH:16])[CH:6]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:8]=1.CC#N>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:8]=1)[CH:15]=[O:16]

Participants

5

Reactant 2

HCID 6342Acetonitrile2×HCID 59817758[3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

Product 1

HCID 598177593-Methoxy-5-(3-methoxy-propoxy)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

The title compound is synthesized by MnO2 oxidation of [3-Methoxy-5-(3-methoxy-propoxy)-phenyl]-methanol (4.20 g, 18.6 mmol) in toluene at RT for 12 h. Yellow oil; MS: 225 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 3.59 min.

Workup

  1. custom3.59 min.

Sources & evidence

ORD record
ord-4d124730a1c54d58ba0158ce2dcc35c2
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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