Acetic Acid → HCID 178450324, compound

HRID 235602Notes

Reaction equation

HRID 235602 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(O)(=O)C.[C:9]([C:14]1[C:15](=[O:33])[CH2:16][CH:17]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[C:23]([CH3:31])[C:22]=2[CH3:32])[CH2:18][C:19]=1[OH:20])(=[O:13])[CH2:10][CH2:11][CH3:12].O>C(OC(=O)C)(=O)C>[C:9]([C:14]1[C:19](=[O:20])[CH2:18][CH:17]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([N+:1]([O-:4])=[O:2])=[C:23]([CH3:31])[C:22]=2[CH3:32])[CH2:16][C:15]=1[OH:33])(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 962WaterHCID 178450311HCID 178450311, compound

Product 1

HCID 178450324HCID 178450324, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of fuming nitric acid (0.42), glacial acetic acid (0.27 g) and acetic anhydride (0.27 g) was added dropwise to a solution of 2-butyryl-5-(2,3-dimethylnaphth-1-yl)-3-hydroxy cyclohex-2-en-1-one (1.5 g) in acetic anhydride (8 ml) at 0° C. The mixture was stirred for 1 hr at 5°-10° C. and at 50° C. for 10 min. The cooled mixture was poured into water (150 ml) which was subsequently extracted with ether. The organic fraction was washed successively with a saturated sodium bicarbonate solution and with water. The dried (Na2SO4) organic extract was evaporated under reduced pressure and the residue was purified by column chromatography over silica with dichloromethane elution to give 2-butyryl-3-hydroxy-5-(2,3-dimethyl-4-nitronapth-1-yl)cyclohex-2-en-1-one a yellow foam. Pmr spectrum (CDCl3 ; δ in ppm): 1.03 (3H,t); 1.49-1.89 (2H,m); 2.40-3.89 (6H,m); 2.37 (3H,s); 2.52 (3H,s); 4.06-4.69 (1H,m); 7.32-7.66 (3H,m); 8.00-8.29 (1H,m); 18.38 (1H,s).

Workup

  1. extractionwas subsequently extracted with ether
  2. washThe organic fraction was washed successively with a saturated sodium bicarbonate solution and with water
  3. dry with materialThe dried (Na2SO4)
  4. extractionorganic extract
  5. customwas evaporated under reduced pressure
  6. customthe residue was purified by column chromatography over silica with dichloromethane elution

Sources & evidence

ORD record
ord-978d17ba36b14ca7b19c4758e6be58ee
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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