HCID 23048955, compound → HCID 10775116, compound

HRID 2106665Notes

Reaction equation

HRID 2106665 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH3:15])[OH:9]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:15][C:14]1[CH:13]=[CH:12][S:11][C:10]=1[C:8](=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 23048955HCID 23048955, compound

Product 1

HCID 10775116HCID 10775116, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

2-Methylphenyl-(3-methyl-2-thienyl)methanol (36.0 g, 0.165 mole) was dissolved in dichloromethane (400 ml) and manganese dioxide (58 g, 0.667 mole) was added. The reaction mixture was heated at reflux for 18 h, cooled and further manganese dioxide (30 g, 0.34 mole) was introduced; reflux was continued for a further 18 h. The mixture was filtered and evaporated to a residue (32 g) which was distilled in vacuo (0.2 mm Hg). Fractions boiling at 100°-120° C. (4.8 g) and 120°-132° C. (21.0 g) were collected, giving the title compound as an oil (25.8 g, 72%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. temperaturereflux
  5. filtrationThe mixture was filtered
  6. customevaporated to a residue (32 g) which
  7. distillationwas distilled in vacuo (0.2 mm Hg)
  8. customFractions boiling at 100°-120° C. (4.8 g) and 120°-132° C. (21.0 g) were collected

Sources & evidence

ORD record
ord-63dcfd61da2e4023a775ca8849e647ce
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

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