m-Chloroperbenzoic acid → HCID 19884710, compound

HRID 846229Notes

Reaction equation

HRID 846229 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:14]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-:42].[Ca+2].[OH-:44]>C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:24])[CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:14]=2)(=[O:44])=[O:42])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 19884728HCID 19884728, compound

Product 1

HCID 19884710HCID 19884710, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound of Example 46. Step B (330 mg, 0.767 mmoles) was dissolved in chloroform and cooled to 0°. m-Chloroperbenzoic acid (328 mg, 1.57 mmoles) was added and the reaction stirred for one hour. Calcium hydroxide (195 mg) was added and the reaction stirred for 90 minutes at room temperature. The mixture was filtered and the filtrate evaporated to dryness. The residue crystallized from ethyl acetatehexane to yield the title compound; m.p. 99°-100°.

Workup

  1. temperaturecooled to 0°
  2. stirringthe reaction stirred for 90 minutes at room temperature
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customThe residue crystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-726e57c5eb51454abfc27b6220032fe3
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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