Nitric Acid → HCID 15295563, compound

HRID 1720142Notes

Reaction equation

HRID 1720142 reaction equation
[CH2:1]([C:8]1[CH:22]=[CH:21][C:11]([C:12]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(=O)(=O)(O)O.[N+:28]([O-])([OH:30])=[O:29]>>[N+:28]([C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:8]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:12]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:13])([O-:30])=[O:29]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 15295558HCID 15295558, compound

Product 1

HCID 15295563HCID 15295563, compound

Procedure

5-(4-n-heptylbenzoyl)pentanoic acid (30.5 g; 0.1 mole) is added slowly to concentrated sulfuric acid (3 ml) while maintaining the mixture temperature below 5° C. with external cooling. A mixture of concentrated nitric acid (8 ml) and sulfuric acid (12 ml) is added dropwise over one hour with the reaction temperature maintained below 5° C. The reaction mixture is poured into ice water (1 liter). The precipitate is collected, dissolved in 2N potassium hydroxide (200 ml), diluted with water (to 400 ml) and washed with ether (2×100 ml). The aqueous phase is acidified with concentrated hydrochloric acid and the product extracted with ether (3×150 ml). The ether solution is dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on a silica gel column (hexane: ether: acetic acid, 74:25:1) to give 5-(3-nitro-4-n-heptylbenzoyl)pentanoic acid (5.25 g) which on recrystallization from heptane is obtained as pale yellow crystals, m.p. 53°-56° C.

Workup

  1. temperaturewhile maintaining the mixture temperature below 5° C. with external cooling
  2. additionis added dropwise over one hour with the reaction temperature
  3. temperaturemaintained below 5° C
  4. customThe precipitate is collected
  5. dissolutiondissolved in 2N potassium hydroxide (200 ml)
  6. additiondiluted with water (to 400 ml)
  7. washwashed with ether (2×100 ml)
  8. extractionthe product extracted with ether (3×150 ml)
  9. dry with materialThe ether solution is dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is chromatographed on a silica gel column (hexane: ether: acetic acid, 74:25:1)

Sources & evidence

ORD record
ord-22bc13fdfafa40f1ad92491dc6b0e9b3
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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