m-Chloroperbenzoic acid → HCID 69963736, compound

HRID 263408Notes

Reaction equation

HRID 263408 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][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=1)([OH:3])=[O:2].C1C=C(Cl)C=C(C(OO)=[O:35])C=1>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][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[CH:11][CH:10]=[C:9]([CH3:26])[N+:8]=1[O-:35])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19038008HCID 19038008, compound

Product 1

HCID 69963736HCID 69963736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-methylpyridine (13.6 g, 38.2 mmol) was dissolved in dry CH2Cl2 (100 mL,) and cooled to 0° C. To this was added 50% mCPBA (13.2 g, 38.3 mmol) in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 h at room temperature. The reaction was poured into aqueous NaHCO3 and the product extracted into CH2Cl2. The organic extract was washed with H2O and brine and dried (MgSO4). The crude product was obtained as a yellow solid and was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured into aqueous NaHCO3
  3. extractionthe product extracted into CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with H2O and brine
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0b04dc76601044bdba901b5b3f9ad1b8
Source dataset
uspto-grants-1997_07
Patent number
US05643914

Reaction notes

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