Dichloromethane → HCID 54569902, compound

HRID 2399342Notes

Reaction equation

HRID 2399342 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27].[C:28]([O-:31])([OH:30])=O.[Na+].ClCCl>O>[C:28]([CH2:3][C@H:4]1[CH2:27][C@@H:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])[O:10][C:8]1=[O:9])([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19387362HCID 19387362, compound

Product 1

HCID 54569902HCID 54569902, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (50% grade, 1.38 g, 4.01 mmol) was added in portions to a vigorously stirred mixture of 8-(2,4-dichlorophenyl)-1-octene (687 mg, 2.67 mmol), saturated aqueous NaHCO3 (15 ml), and dichloromethane (10 ml) at 0° C. The mixture was stirred for 5 min at 0° C., at room temperature for 1 h, then poured into water, and extracted with ether. The extracts were washed with aqueous Na2SO3 /NaHCO3, water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum and the residue purified by chromatography on silica gel (5-20% ether/petroleum ether 40°-60° C.) to give the title compound (265 mg, 25%, 3 steps) as an oil.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with aqueous Na2SO3 /NaHCO3, water, saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under vacuum
  5. customthe residue purified by chromatography on silica gel (5-20% ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-292cf08c4cd147b3a95de5eaca151e36
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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