1,4-Cyclohexanedione → HCID 57805450, compound

HRID 2104939Notes

Reaction equation

HRID 2104939 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=O)[C:5](=[CH:8][C:9]=1[F:10])[CH:6]=O.[C:13]1(=[O:20])[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[C:9]([F:10])=[CH:8][C:5]2[C:4](=[CH:11][C:18]3[C:13](=[O:20])[C:14]4[C:15]([C:16](=[O:19])[C:17]=3[CH:6]=2)=[CH:11][C:4]2[C:5](=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=2)[CH:6]=4)[CH:3]=1

Participants

5

Reactant 3

HCID 125111,4-CyclohexanedioneHCID 14798Sodium HydroxideHCID 226289074,5-Difluoro-1,2-benzenedicarboxaldehyde2×

Product 1

HCID 57805450HCID 57805450, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,5-difluorophthalaldehyde (Compound 22)(0.48 g, 2.8 mmol, 2 molar equivalents) and 1,4-cyclohexanedione (0.16 g, 1.4 mmol, 1 molar equivalent) in ethanol (40 ml) was added a solution of 5% aqueous NaOH (0.6 ml) at room temperature. The reaction mixture was stirred for 30 minutes at room temperature and then warmed to 60° C. After 1 hour at 60° C., the reaction mixture was cooled to room temperature. The resulting precipitate was filtered, washed with water (15 ml), ethanol (30 ml) and diethyl ether (30 ml) to give the title compound as a yellow powder (0.35 g, 64%) used as obtained.

Workup

  1. temperaturewarmed to 60° C
  2. waitAfter 1 hour at 60° C.
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water (15 ml), ethanol (30 ml) and diethyl ether (30 ml)

Sources & evidence

ORD record
ord-309e2277b6294e41b8a563b0496216d1
Source dataset
uspto-grants-2009_08
Patent number
US07576208B2

Reaction notes

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