m-Chloroperbenzoic acid → HCID 67711257, compound

HRID 2257077Notes

Reaction equation

HRID 2257077 reaction equation
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=1)([OH:3])=[O:2].ClC1C=C(C=CC=1)C(OO)=[O:32].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=[C:9]([CH3:26])[N+:8]=1[O-:32])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19027969HCID 19027969, compound

Product 1

HCID 67711257HCID 67711257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-methylpyridine (2.15 g, 5.95 mmol) was dissolved in dry CH2Cl2 (20 mL) and cooled to 0∞C; 85% m-chloroperoxybenzoic acid (1.45 g, 7.14 mmol) was added and the reaction was stirred at 0∞C for 30 minutes and at room temperature for 16 hours. The reaction solution was poured into saturated aqueous NaHCO3 (20 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the combined CH2Cl2 extracts were washed with H2O (20 mL) and brine and dried (MgSO4). The crude pale yellow solid was used directly in the next step without further purification: 1H NMR (250 MHz CDCl3): δ8.23 (d, J=16.2 Hz, 1H, olefin), 7.58 (d, J=16.2 Hz, 1H, olefin), 7.13 (d, J=8.8 Hz, 1H, 5-pyridyl), 6.79 (d, J=8.8 Hz, 1H, 4-pyridyl), 4.06 (t, J=6.6 Hz, 2H, OCH2), 3.81 (s, 3H, CO2CH3), 2.45 (s, 3H, CH3), 1.92-0.85 (m, 23H, aliphafic); MS (CI): 378.2 (M+H).

Workup

  1. temperaturecooled to 0∞C
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
  3. washthe combined CH2Cl2 extracts were washed with H2O (20 mL) and brine
  4. dry with materialdried (MgSO4)
  5. customThe crude pale yellow solid was used directly in the next step without further purification

Sources & evidence

ORD record
ord-c1f6b23545284b08b1f0244142608d69
Source dataset
uspto-grants-1997_08
Patent number
US05656636

Reaction notes

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