Water → 3,5-Bis(trifluoromethyl)anisaldehyde

HRID 2177158Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:6]([C:7]#N)=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16].[OH2:19]>C(O)(=O)C.N1C=CC=CC=1.[Ni]>[CH3:1][O:2][C:3]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:6]([CH:7]=[O:19])=[CH:5][C:4]=1[C:15]([F:18])([F:17])[F:16]

Participants

Conditions

Temperature: 45 °C

Procedure

Into a 100-mL round-bottom flask, was placed 4-methoxy-3,5-bis(trifluoromethyl)benzonitrile (868 mg, 3.23 mmol, 1.00 equiv), a solution of NaH2PO2.H2O in water (10.0 mL), acetic acid (10.0 mL), pyridine (20.0 mL), Raney-Ni (0.9 g). The resulting solution was stirred for 3 h at 45° C. in an oil bath. The reaction progress was monitored by GCMS. The solids were filtered out. 20.0 mL EtOAc and 20.0 mL H2O were added into the mixture. The organic phase was washed by H2O with 2*20 mL and dried over Na2SO4. The solvent was removed and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). This resulted in 0.43 g (49%) of 4-methoxy-3,5-bis(trifluoromethyl)benzaldehyde as yellow oil. Mass spectrum (GC, m/z): Calcd. for C10H6F6O2, 272.0 (M). found 272.0.

Workup

customInto a 100-mL round-bottom flask, was placed
filtrationThe solids were filtered out
addition20.0 mL EtOAc and 20.0 mL H2O were added into the mixture
washThe organic phase was washed by H2O with 2*20 mL
dry with materialdried over Na2SO4
customThe solvent was removed
customThis resulted in 0.43 g (49%) of 4-methoxy-3,5-bis(trifluoromethyl)benzaldehyde as yellow oil

Sources & evidence

ORD record: ord-c2926165ffb94089802c48f0d589e0dd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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