m-Chloroperbenzoic acid → HCID 13375397, compound

HRID 1381772Notes

Reaction equation

HRID 1381772 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.ClC1C=CC=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 RB flask fitted with addition funnel and stirring bar was charged with 10-methylthio-9-anthracenecarbaldehyde (example 3A, 12.0 g, 48 mmol) and 450 mL of CH2Cl2. The resulting solution was cooled to 5° with an ice bath. A solution of m-chloroperbenzoic acid (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 a plug of SiO2 (250 g) using PhCH3 (5 L) as the eluting solvent. The desired material was then eluted from the SiO2 using EtOAc (2 L) as 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 RB 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. washThe desired material was then eluted from the SiO2
  8. additiondiluted to 700 mL with hexane
  9. filtrationThe resulting yellow solid was filtered
  10. customdried at 50°

Sources & evidence

ORD record
ord-707eb071b75c453dbc33c7bb889ecb10
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

Loading…