Potassium Carbonate → 3,5-Dimethyl-4-(4-trifluoromethyl-benzyloxy)-benzaldehyde

HRID 558165Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[OH:13][C:14]1[C:21]([CH3:22])=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=1[CH3:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:23][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH3:22])[C:14]=1[O:13][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1)[CH:18]=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

0.5M solution of 1-bromomethyl-4-trifluoromethyl-benzene (1.9 g, 8.0 mmol) in DMF was added dropwise to a suspension of 4-hydroxy-3,5-dimethyl-benzaldehyde (930 mg, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (120 mg, 0.73 mmol) in DMF (100 ml). The reaction mixture was stirred at 90° C. overnight. After cooling, the solid residue was filtered off and the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate and the organic layer washed twice with NaOH 1M, dried over Na2SO4 and evaporated to dryness. The residue was purified on silica gel, obtaining 2.24 g of the title compound in a quantitative yield.

Workup

temperatureAfter cooling
filtrationthe solid residue was filtered off
customthe solvent was evaporated under vacuum
dissolutionThe residue was dissolved in ethyl acetate
washthe organic layer washed twice with NaOH 1M
dry with materialdried over Na2SO4
customevaporated to dryness
customThe residue was purified on silica gel

Sources & evidence

ORD record: ord-93ace4af93f845c7a489c170a7953c0a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063039B2

Reaction notes

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