1,4-Cyclohexanedione → HCID 57805450, compound

HRID 1644013Notes

Reaction equation

HRID 1644013 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-a4cac5d51f224868b5870a8bf20f1bfc
Source dataset
uspto-grants-2012_02
Patent number
US08119804B2

Reaction notes

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