Hydrochloric Acid → 4-Methoxy-3-({[4-(trifluoromethyl)benzyl]oxy}methyl)benzaldehyde

HRID 1816576Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:3]=1.C([Li])CCC.[CH:28](N1CCOCC1)=[O:29].Cl>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:28]=[O:29])=[CH:3][C:4]=1[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

1.4 g of 4-bromo-1-methoxy-2-({[4-(trifluoromethyl)benzyl]oxy}methyl)benzene was dissolved in 15 ml tetrahydrofuran and cooled at −78° C., and 3.0 ml n-butyl lithium (1.5 M solution in pentane) was added. After stirring the reaction mixture at −78° C. for 30 minutes, 0.45 ml N-formyl morpholine was added, and the mixture was stirred at −78° C. for 1 hour. 1N hydrochloric acid was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 0.42 g of 4-methoxy-3-({[4-(trifluoromethyl)benzyl]oxy}methyl)benzaldehyde was obtained.

Workup

stirringthe mixture was stirred at −78° C. for 1 hour
extractionby extracting with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
washfrom fractions eluted with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record: ord-79ccf53dcb694f4999e983a8f8f0ef1b
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884821B1

Reaction notes

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