Hydrochloric Acid → HCID 54015350, compound

HRID 2257445Notes

Reaction equation

HRID 2257445 reaction equation
[CH3:1][C@H:2]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O-:21][Mn](=O)(=O)=O.[K+].[O-]S([O-])=O.[Na+].[Na+].Cl>CC(C)=O.O>[CH3:1][C@H:2]([O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]([OH:21])=[O:15])=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 54229065HCID 54229065, compound

Product 1

HCID 54015350HCID 54015350, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 1.086 g (3.89 mmol) of (S)-4-(1-methylheptyloxy)-2-nitrobenzaldehyde in 40 ml of acetone was added a solution of KMnO4 (0.984 g, 6.23 mmol) in 47 ml of water dropwise. The reaction mixture was stirred at room temperature for 6 h and then treated with 5% Na2SO3 (100 ml), acidified with conc. HCl (pH: 4-5), and the resulting solution was extracted with ethyl ether several times. The organic extract was concentrated and extracted with 10% NaOH solution. The alkaline extract was washed with ether, acidified with conc. HCl/ice, and the resulting solution extracted with ethyl ether. The organic layer was washed with water, dried, and the solvent evaporated. (S)-4-(1-Methylheptyloxy)-2-nitrobenzoic acid (Compound 37, Scheme VI, R1 =(S)-OCH(CH3)C6H13) was obtained as a dark orange liquid (0.8 g, 70% ) which was used in the next step without further purification; Rf [hexanes/ethyl acetate 70/30+1 drop of acetic acid]: 0.16; 1H NMR (300 MHz, CDCl3): δ 0.86(t, 3H, J=6.8 Hz), 1.16-1.48(m, 8H), 1.32(d, 3H, J=5.(Hz), 1.60(m, 1H), 1.72(m, 1H) 4.45(m, 1H), 7.02(dd, 1H, J=2.4 Hz J=8.8 Hz), 7.09(d, 1H, J=2.4 Hz), 7.90(d, 1H, J=8.8 Hz); 13C NMR (300 MHz, CDCl3): δ 13.98, 19.22, 22.51, 25.24, 29.14, 31.68, 36.14, 79.94, 110.26, 117.84, 118.98, 132.97, 150.69, 160.61, 170.81; Mass spectrum, m/z(rel.intensity): 295(M+ 1), 265(9), 166(8), 135(36), 112(14), 71(66), 57(100), 55(27), 43(94), 41(69).

Workup

  1. extractionthe resulting solution was extracted with ethyl ether several times
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. extractionextracted with 10% NaOH solution
  5. extractionThe alkaline extract
  6. washwas washed with ether
  7. extractionthe resulting solution extracted with ethyl ether
  8. washThe organic layer was washed with water
  9. customdried
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-4e905df5551246398659bc35919c0cb8
Source dataset
uspto-grants-1997_08
Patent number
US05658493

Reaction notes

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