m-Chloroperbenzoic acid → HCID 13520251, compound

HRID 485103Notes

Reaction equation

HRID 485103 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[C:3]([CH:16]=[O:17])[CH:2]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[Ca+2].[OH-]>C(Cl)Cl>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6](=[O:26])[C:5]=2[CH:4]=[C:3]([CH:16]=[O:17])[CH:2]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 13520250HCID 13520250, compound

Product 1

HCID 13520251HCID 13520251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mix 2.84 g (11.83 mmole) of 10,11-dihydrodibenzo[b,f]thiepin-3-carboxaldehyde with 90 ml methylene chloride at 0° C. Add 2.3 g (11.33 mmoles) of 85% m-chloroperbenzoic acid, followed by the addition of 100 ml methylene chloride. Stir for 2 hours, and then add 4.6 g calcium hydroxide to the resulting clear solution at room temperature. After stirring the suspension for 15 minutes, filter to remove the inorganic solid, and evaporate the filtrate containing the dissolved product to dryness, producing as a residue a dry solid comprising the title product. Purify by recrystallization from acetonitrile, m.p. 158.5°-160° C.

Workup

  1. stirringAfter stirring the suspension for 15 minutes
  2. filtrationfilter
  3. customto remove the inorganic solid
  4. customevaporate the filtrate
  5. additioncontaining the dissolved product to dryness

Sources & evidence

ORD record
ord-aecfb0bfd5ef4c4eae0f7ceec5209340
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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