Formic Acid → 3-Methoxy-5-(trifluoromethyl)benzaldehyde

HRID 217508Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#N.C(O)=[O:16]>O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[O:16]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-methoxy-5-(trifluoromethyl)benzonitrile (88 mg, 0.43 mmol) and PtO2 (9.8 mg, 0.043 mmol) in 88% formic acid (651 μL) was heated to 60° C. The reaction was stirred at this temperature for thirty minutes. The reaction was then cooled to room temperature, diluted with hexanes (5 mL), loaded on a silica gel column, and purified with 1% to 15% EtOAc/hexanes to afford 3-methoxy-5-(trifluoromethyl)benzaldehyde. Rf=0.56 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.01 (s, 1H), 7.71 (s, 1H), 7.56 (s, 1H), 7.39 (s, 1H), 3.92 (s, 3H).

Workup

temperatureThe reaction was then cooled to room temperature
custompurified with 1% to 15% EtOAc/hexanes

Sources & evidence

ORD record: ord-bf448e1d38ef4a8990a80ceddddc9275
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193365B2

Reaction notes

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