m-Chloroperbenzoic acid → HCID 13375397, compound

HRID 1381735Notes

Reaction equation

HRID 1381735 reaction equation
[CH3:1][S:2][C:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH:17]=[O:18])=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2)=[O:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13375392HCID 13375392, compound

Product 1

HCID 13375397HCID 13375397, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 L round bottom flask fitted with addition funnel and stirring bar was charged with 10-methylthio-9-anthracenecarbaldehyde (example 6A, 12.0 g, 48 mmol) and 450 mL of CH2Cl2. The resulting solution was cooled to 5° with an ice bath. A solution of MCPBA (Aldrich (85%), 9.64 g, 48 mmol) in 350 mL of CH2Cl2 was then added dropwise to the flask over 1 h. The reaction mixture was allowed to warm to RT over 1 h and then was washed with 5% NaHCO3 solution (2×500 mL), dried (Na2SO4), filtered, concentrated to 500 mL, and passed through SiO2 (250 g) using PhCH3 (5 L) eluting solvent. The desired material was then eluted from the SiO2 using EtOAc (2 L) as the eluting solvent. The solvent volume was reduced to 100 mL and then diluted to 700 mL with hexane. The resulting yellow solid was filtered and dried at 50° to give 11.98 g (94% of 10-methylsulfinyl-9-anthracenecarbaldehyde mp 182°-184°, (C, H, S).

Workup

  1. customA 1 L round bottom flask fitted with addition funnel
  2. temperatureThe resulting solution was cooled to 5° with an ice bath
  3. washwas washed with 5% NaHCO3 solution (2×500 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to 500 mL
  7. washeluting solvent
  8. washThe desired material was then eluted from the SiO2
  9. additiondiluted to 700 mL with hexane
  10. filtrationThe resulting yellow solid was filtered
  11. customdried at 50°

Sources & evidence

ORD record
ord-cae1484e44d64c0886687682c8e74bb1
Source dataset
uspto-grants-1989_02
Patent number
US04803226

Reaction notes

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