Acetone → HCID 5463280, compound

HRID 705463Notes

Reaction equation

HRID 705463 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O.[CH3:12][C:13]([CH3:15])=[O:14]>O.CCO>[Cl:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1/[CH:6]=[CH:12]/[C:13](=[O:14])/[CH:15]=[CH:6]/[C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[Cl:3]

Participants

6

Reactant 3

HCID 180AcetoneHCID 69962-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 5463280HCID 5463280, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (1.4 g, 142 mmol) in H2O (60 mL) and EtOH (60 mL) was added to a mixture of 2-chlorobenzaldehyde (8 mL, 72 mmol) in acetone (2.6 mL, 36 mmol). The reaction mixture was stirred for 1d at room temperature and the resulting precipitate was filtered, washed with H2O, recrystallized from EtOAc and dried in vacuo to obtain NW268 as a bright yellow solid (7.4 g, 69%). mp: 107-109° C. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.15 (d, 3J=16.0 Hz, 2H, Hvin), 7.79-7.66 (m, 2H, HAr), 7.51-7.29 (m, 6H, HAr), 7.08 (d, 3J=16.0 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.7 (C), 139.3 (CH), 135.4 (C), 133.0 (C), 131.2 (CH), 130.2 (CH), 127.7 (CH), 127.5 (CH), 127.1 (CH). MS (FAB) m/z: 303.1 (M+). Anal. calcd for C17H12Cl2O: C, 67.35; H, 3.99; Cl, 23.39. Found: C, 67.09; H, 4.06; Cl, 22.65%.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with H2O
  3. customrecrystallized from EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-51dd42c33d584aa49c3588fb324e83dc
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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