Acetone → HCID 20348544, compound

HRID 705464Notes

Reaction equation

HRID 705464 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[CH3:14][C:15]([CH3:17])=[O:16]>CCO.O.[OH-].[Na+]>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:11]/[C:4](=[O:3])/[CH:5]=[CH:6]/[C:7]2[CH:10]=[CH:17][C:15]([O:16][C:2]([F:1])([F:12])[F:13])=[CH:14][CH:8]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 180AcetoneHCID 69573p-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 20348544HCID 20348544, compoundYield 26.3%

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A colorless solution of 4-(trifluoromethoxy)-benzaldehyde (0.75 mL, 5.3 mmol) in acetone (0.19 mL, 2.6 mmol), EtOH (5 mL) and H2O (1 mL) was treated with aq. 10% NaOH solution (˜12 drops). The reaction mixture was stirred for 2 h at room temperature and the colorless solution turned into a yellow suspension. The precipitate was filtered, washed with H2O and dried in vacuo to obtain NW254 as a pale yellow solid (275 mg, 25%). mp: 112-115° C. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.74 (d, 3J=16.1 Hz, 2H, Hvin), 7.67 (d, 3J=8.5 Hz, 4H, HAr), 7.28 (d, 3J=8.2 Hz, 4H, HAr), 7.06 (d, 3J=15.9 Hz, 2H, Hvin.). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.2 (C), 150.6 (C), 141.8 (CH), 133.3 (C), 129.8 (CH), 126.0 (CH), 121.2 (CH). MS (EI) m/z: 402.1 (M+). Anal. calcd for C19H12F6O3: C, 56.73; H, 3.01. Found: C, 56.44; H, 3.10%.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-23e5eb0e44204e008db5fc40d2b30e5b
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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