m-Chloroperbenzoic acid → HCID 67711243, compound

HRID 2257081Notes

Reaction equation

HRID 2257081 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][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:11][CH:10]=[C:9]([CH3:30])[N:8]=1)([OH:3])=[O:2].C1C=C(Cl)C=C(C(OO)=[O:39])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][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[CH:11][CH:10]=[C:9]([CH3:30])[N+:8]=1[O-:39])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19027947HCID 19027947, compound

Product 1

HCID 67711243HCID 67711243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
13 °C

Procedure

2-(E-2-Carboxymethylethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-methylpyridine (17.1 g, 41.5 mmol) was dissolved in dry CH2Cl2 (105 mL) and cooled to 13° C.; 50% mCPBA (15.8 g, 45.8 mmol) was added in three portions over 10 minutes. The cooling bath was removed and the reaction was stirred for 15 hours 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-c9ef1db1f4494d85bcbdbba37cc07585
Source dataset
uspto-grants-1997_08
Patent number
US05656636

Reaction notes

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