Acetic Acid → HCID 178458845, compound

HRID 477403Notes

Reaction equation

HRID 477403 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(=O)C.[C:9]([C:13]1[C:14](=[O:29])[CH2:15][CH:16]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[CH2:17][C:18]=1[OH:19])(=[O:12])[CH2:10][CH3:11]>C(OC(=O)C)(=O)C>[C:9]([C:13]1[C:18](=[O:19])[CH2:17][CH:16]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([N+:1]([O-:4])=[O:2])[C:21]=2[CH3:28])[CH2:15][C:14]=1[OH:29])(=[O:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 178458835HCID 178458835, compound

Product 1

HCID 178458845HCID 178458845, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

A solution of fuming nitric acid (2.17 ml), glacial acetic acid (1.98 ml) and acetic anhydride (1.94 ml) was added dropwise to a solution of 2-propionyl-3-hydroxy-5-mesitylcyclohex-2-en-1-one (10 g, 34.9 mmol) in acetic anhydride (23.3 ml) at 5°. Stirring was continued at 5° for 1 hr, then at 20° for 2 hr and 50° for 10 min. The mixture was then cooled and poured into ice water. The aqueous solution was extracted with methylene chloride. The organic layer was washed with water; saturated sodium bicarbonate solution and then further water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 2-propionyl-3-hydroxy-5-(3-nitro-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a pale yellow solid (9.59 g, 83%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm): 1.15 (3H,t), 2.18 (3H,s); 2.24 (3H,s); 2.38 (3H,s); 2.4-4.1 (7H,m); 6.88 (1H,s); 18.20 (1H,s).

Workup

  1. waitat 20° for 2 hr
  2. wait50° for 10 min
  3. temperatureThe mixture was then cooled
  4. extractionThe aqueous solution was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialsaturated sodium bicarbonate solution and then further water, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55fd436694d54cdea97c24a0d727efbe
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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