6-Methoxy-2-phenyl-5-hydroxymethylbenzothiazole → 6-Methoxy-2-phenyl-benzothiazol-5-aldehyde

HRID 1459599Notes

Reaction equation

HRID 1459599 reaction equation
[CH3:1][O:2][C:3]1[C:17]([CH2:18][OH:19])=[CH:16][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1>CC(CC(C)C)=O.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:17]([CH:18]=[O:19])=[CH:16][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 226200816-Methoxy-2-phenyl-5-hydroxymethylbenzothiazole

Product 1

HCID 226200646-Methoxy-2-phenyl-benzothiazol-5-aldehydeYield 22.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 10.94 grams (40.4 mmol) 6-methoxy-2-phenyl-5-hydroxymethylbenzothiazole (as part of a mixture of regioisomeric alcohols) in 600 mL of methylisobutyl ketone was treated with 42 grams (484 mmol) of manganese dioxide. The mixture was heated under reflux for 1.5 hours and was then filtered through Celite®. The filtrate was evaporated in vacuo and the residue was chromatographed on silica (elution with 9/1 hexane/ethyl acetate). Mixed fractions were rechromatographed on silica using 95/5 hexane/ethyl acetate to afford a total of 2.43 grams of the desired aldehyde.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationwas then filtered through Celite®
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was chromatographed on silica (elution with 9/1 hexane/ethyl acetate)
  6. customMixed fractions were rechromatographed on silica using 95/5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c86ec66dae2d48d7b0ac3e2d0a2754cf
Source dataset
uspto-grants-1998_12
Patent number
US05854262

Reaction notes

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