m-Chloroperbenzoic acid → HCID 18948434, compound

HRID 1768589Notes

Reaction equation

HRID 1768589 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)Cl>[O:31]1[CH2:22][CH:21]1[CH2:20][CH:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18948412HCID 18948412, compound

Product 1

HCID 18948434HCID 18948434, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 12.92 g (43.6 mmole) of t-butyl 2-(1-naphthylmethyl)-4-pentenoate (prepared as described in Preparation 10), 11.29 g (65.4 mmole) of m-chloroperbenzoic acid and 100 ml of methylene chloride was stirred at room temperature for 24 hours. At the end of this time, the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 5: 95 by volume mixture of methanol and methylene chloride), to afford 4.57 g (33.6%) of the title compound as a pale yellow oil.

Workup

  1. washAt the end of this time, the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, in that order
  2. dry with materialafter which it was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel (eluent
  5. additiona 5: 95 by volume mixture of methanol and methylene chloride),

Sources & evidence

ORD record
ord-ee3d153457024fc6bc08999f14fc3357
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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