Sodium Hydroxide → HCID 178458842, compound

HRID 477404Notes

Reaction equation

HRID 477404 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([C:13]1[C:14](=[O:32])[CH2:15][CH:16]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([N+:28]([O-])=O)[C:21]=2[CH3:31])[CH2:17][C:18]=1[OH:19])(=[O:12])[CH2:10][CH3:11].[OH-].[Na+]>C(O)C>[C:9]([C:13]1[C:14](=[O:32])[CH2:15][CH:16]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([NH2:28])[C:21]=2[CH3:31])[CH2:17][C:18]=1[OH:19])(=[O:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 178458845HCID 178458845, compound

Product 1

HCID 178458842HCID 178458842, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium dithionite (27.74 g, 159 mmol) was added over a period of 30 min to a refluxing solution of 2-propionyl-3-hydroxy-5-(3-nitro-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (9.59 g, 28.9 mmol) and sodium hydroxide (1.10 g, 27.5 mmol) in 50% aqueous ethanol (350 ml). Refluxing was continued for 1 hr. The hot mixture was filtered, neutralized with dilute hydrochloric acid and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to yield the crude 2-propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a brown oil (3.0 g, 34%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm): 1.17 (3H,t); 2.12 (3H,s); 2.20 (3H,s); 2.25 (3H,s); 2.3-4.2 (7H,m); 6.72 (1H,s).

Workup

  1. temperatureRefluxing
  2. filtrationThe hot mixture was filtered
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-001a51eca479475bab867fa6a9f7ac0b
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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