Water → HCID 20389879, compound

HRID 426768Notes

Reaction equation

HRID 426768 reaction equation
[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[S:13][CH:14]=[CH:15][C:4]=2[CH:3]1O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[S:13][CH:14]=[CH:15][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 20389846HCID 20389846, compound

Product 1

HCID 20389879HCID 20389879, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

24.8 g (0.1 mole) of 4,5-dihydro-5-methyl-benzo[f]thieno [2,3-b]thiepin-4-ol in 600 ml of benzene is boiled, with the addition of 0.57 g (0.03 mole) of p-toluenesulphonic acid hydrate, for one hour on a water separator. The solution is thereupon cooled to 20°, extracted by shaking with 2 N sodium bicarbonate solution, dried over sodium sulphate and concentrated in vacuo. The oily residue is chromatographed on a silica-gel column (300 g of silica gel, particle size 0.063-0.2 mm) with the use of cyclohexane as the eluant. Recrystallisation of the eluted substance from pentane yields 5-methyl-benzo[f]thieno[2,3-b]thiepin, m.p. 70°-71°.

Workup

  1. temperatureThe solution is thereupon cooled to 20°
  2. extractionextracted
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue is chromatographed on a silica-gel column (300 g of silica gel, particle size 0.063-0.2 mm) with the use of cyclohexane as the eluant
  6. customRecrystallisation of the eluted substance from pentane

Sources & evidence

ORD record
ord-db8a3017b5c046aab36c0e9700c9436a
Source dataset
uspto-grants-1979_10
Patent number
US04171366

Reaction notes

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