Acetone → HCID 59612093, compound

HRID 889643Notes

Reaction equation

HRID 889643 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-20cdbf3b64c74a0f88fdadd8b4770521
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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