Sodium Hydroxide → 3-Methoxy-4-(trifluoromethyl)benzaldehyde

HRID 1375018Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:6](N(OC)C)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[C:15]([F:16])([F:17])[F:18])[CH:6]=[O:7]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred solution of 3-methoxy-N-methoxy-N-methyl-4-(trifluoromethyl)benzamide (2.63 g) in dry tetrahydrofuran (26 ml) was added lithium aluminum hydride (380 mg) at −40° C. under nitrogen atmosphere. After 1 hour of stirring at 5° C., 2N sodium hydroxide was added to the mixture. The insoluble materials were removed by filtration through Celite® and washed with ethyl acetate. The filtrate and washing were combined and evaporated under reduced pressure to give crude 3-methoxy-4-(trifluoromethyl)benzaldehyde as a colorless oil.

Workup

customThe insoluble materials were removed by filtration through Celite®
washwashed with ethyl acetate
washThe filtrate and washing
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-be450ddaf6e740b3a0d5466153396b8f
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166598B2

Reaction notes

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