(3-Chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)methanol → 3-Chloro-5,6-dimethoxy-benzo[b]thiophene-2-carbaldehyde

HRID 1004115Notes

Reaction equation

HRID 1004115 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]>C1(C)C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 1

HCID 10956261(3-Chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)methanol

Product 1

HCID 117801503-Chloro-5,6-dimethoxy-benzo[b]thiophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 1140TolueneSolvent

Procedure

96 mmol (1.6 equivalents) of MnO2 are added at room temperature under an inert atmosphere to a suspension of 60.4 mmol of the compound obtained in Step C in 360 ml of toluene. After 6 hours' reaction at 80° C., 0.6 equivalent of MnO2 is added to the reaction mixture, followed six hours later by 0.6 equivalent of MnO2. The reaction mixture is then filtered while hot over Celite and rinsed with toluene. After 12 hours at room temperature, the filtrate precipitates. Filtration of the precipitate followed by rinsing with toluene and then with pentane enables 8.65 g of the expected product to be isolated.

Workup

  1. customAfter 6 hours' reaction at 80° C.
  2. filtrationThe reaction mixture is then filtered while hot over Celite
  3. washrinsed with toluene
  4. customthe filtrate precipitates
  5. filtrationFiltration of the precipitate
  6. washby rinsing with toluene
  7. customto be isolated

Sources & evidence

ORD record
ord-4fa270bd9fc647eead3cdabb8f362ef4
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Reaction notes

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