Sodium Carbonate → 9-Phenylnonanohydroxamic acid

HRID 1723404Notes

Reaction equation

HRID 1723404 reaction equation
[C:1]1([CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.Cl.[NH2:23][OH:24].[C:25](=[O:28])([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[C:1]1([CH2:7][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:25]([NH:23][OH:24])=[O:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 19609332HCID 19609332, compound

Product 1

HCID 1883829-Phenylnonanohydroxamic acidYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

Into a 100 ml, 3 neck flask equipped with thermometer, drying tube, stirrer and dropping funnel is placed phenylnonanoic acid (10 gms, 0.0426 mole) and methylene chloride (20 ml). The resulting stirred mixture is cooled to 5° and thionyl chloride (6.2 gms, 0.052 mole) is added dropwise during 5 minutes, then stirred at room temperature for 18 hours. The methylene chloride and excess thionyl chloride are removed in vacuo to an oil, 10.8 gms (100%). This is diluted with methylene chloride (15 ml) and then added to a stirred mixture of hydroxylamine hydrochloride (3.6 gms, 0.052 mole), anhydrous sodium carbonate (5 gms, 0.052 mole) and methylene chloride (60 ml). During the addition, the temperature of the reaction is maintained between 5°-10° by regulating the addition. After stirring this mixture for 1/2 hour, water (6 ml) is added dropwise during 5 minutes, then the mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with methylene chloride (60 ml) and water (30 ml). The organic layer is separated and washed with water (2×30 ml), brine (2×30 ml), and dried over magnesium sulfate, then filtered and concentrated in vacuo to a solid residue. One recrystallization from methylene chloride (100 ml) gives 6.7 gms (63%) of pure title product, m.p. 75°-7°.

Workup

  1. customInto a 100 ml, 3 neck flask equipped with thermometer
  2. customdrying tube, stirrer
  3. temperatureis cooled to 5°
  4. stirringstirred at room temperature for 18 hours
  5. customThe methylene chloride and excess thionyl chloride are removed in vacuo to an oil, 10.8 gms (100%)
  6. additionThis is diluted with methylene chloride (15 ml)
  7. additionDuring the addition
  8. temperaturethe temperature of the reaction is maintained between 5°-10°
  9. additionthe addition
  10. stirringAfter stirring this mixture for 1/2 hour
  11. stirringthe mixture is stirred at room temperature for 18 hours
  12. customThe organic layer is separated
  13. washwashed with water (2×30 ml), brine (2×30 ml)
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo to a solid residue
  17. customOne recrystallization from methylene chloride (100 ml)

Sources & evidence

ORD record
ord-35ac9ea7d272410b97ddc98473352c9e
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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