Acetone → HCID 59612093, compound

HRID 1907114Notes

Reaction equation

HRID 1907114 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[OH-].[Na+].ClCCl.[CH3:16][C:17]([CH3:19])=[O:18]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:16]/[C:17](=[O:18])[CH3:19])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 59612093HCID 59612093, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mechanically stirred solution of 4-chloro-2-fluorobenzaldehyde (23.8 grams (g), 0.15 mole (mol)) in acetone (100 milliliters (mL)) at room temperature was added over 20 minutes (min) a solution of sodium hydroxide (NaOH, 6.6 g, 0.165 mol) in water (H2O, 400 mL). After stirring the reaction mixture overnight, dichloromethane (CH2Cl2, 100 mL) was added. The aqueous layer was separated and extracted with CH2Cl2 (100 mL), and the combined organic extracts were washed with brine and dried over magnesium sulfate (MgSO4). Solvent removal followed by Kugelrohr distillation gave 4-(4-chloro-2-fluorophenyl)-3-buten-2-one (1; 22.5 g, 76%) as a colorless liquid, which solidified upon standing: by 70-80° C., 0.1 mmHg (13.33 pascals (Pa)); 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=16.5 Hz, 1H), 7.50 (t, J=8.1 Hz, 1H), 7.22-7.12 (m, 2H), 6.76 (d, J=16.5 Hz, 1H), 2.39 (s, 3H); HRMS-ESI (m/z): calcd for C10H8ClFO, 198.024. found 198.025.

Workup

  1. additionwas added
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2 (100 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate (MgSO4)
  6. customSolvent removal
  7. distillationfollowed by Kugelrohr distillation

Sources & evidence

ORD record
ord-99653acb62be4fa7bc5b3a51f1f9ce0e
Source dataset
uspto-grants-2013_12
Patent number
US08598086B2

Reaction notes

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