m-Chloroperbenzoic acid → HCID 53646573, compound

HRID 2399339Notes

Reaction equation

HRID 2399339 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[C:18](/[C:24]([O:26]C)=[O:25])\[CH2:19][C:20]([O:22]C)=[O:21].ClC1C=CC=C(C(OO)=[O:36])C=1.C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[C:24]([C@:18]1([OH:36])[C@@H:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[O:21][C:20](=[O:22])[CH2:19]1)([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 18470521Sodium bicarbonate sodium sulfiteHCID 19387365HCID 19387365, compound

Product 1

HCID 53646573HCID 53646573, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-Methyl 12-(2,4-dichlorophenyl)-3-methoxycarbonyl-3-dodecenoate (686 mg, 1.65 mmol, described in example 4) and 3-chloroperbenzoic acid (5.7 g of 55% grade, 18.2 mmol) were heated under reflux in dichloromethane (15 ml) for 24 h. The mixture was cooled and poured into aqueous NaHCO3 /Na2SO3. This mixture was stirred for 10 min, then extracted with dichloromethane. The extracts were washed with aqueous NaHC3, water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum, and the residue purified by chromatography on silica gel (20-40% ether/petroleum ether 40-60%) to give the title compound (369 mg, 52%) as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane
  3. washThe extracts were washed with aqueous NaHC3, water, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under vacuum
  6. customthe residue purified by chromatography on silica gel (20-40% ether/petroleum ether 40-60%)

Sources & evidence

ORD record
ord-2ca44bc3afe546c0b1697826ace955c9
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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