p-Toluenesulfonic acid monohydrate → 4-Ethyl-7-methyl-benzo[b]thiophen-5-ol

HRID 38427Notes

Reaction equation

HRID 38427 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([CH2:13][CH3:14])[C:7](=[O:12])[CH2:8][C:9](=O)[CH3:10])=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)C>[CH2:13]([C:6]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[C:9]([CH3:10])=[CH:8][C:7]=1[OH:12])[CH3:14]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 595986385-Thiophen-3-yl-heptane-2,4-dione

Product 1

HCID 595987024-Ethyl-7-methyl-benzo[b]thiophen-5-ol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

5-Thiophen-3-yl-heptane-2,4-dione (410 mg, 2 mmol) was dissolved in 15 ml benzene, and p-toluene sulfonic acid monohydrate (408 mg, 2 mmol) was added. The reaction mixture was heated to reflux for 30 min, cooled, diluted with diethy ether, washed with saturated sodium bicarbonate, water, brine, and dried over magnesium sulfate. Concentration in vacuo 370 mg of 4-Ethyl-7-methyl-benzo[b]thiophen-5-ol, 98%, as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. temperaturecooled
  4. washwashed with saturated sodium bicarbonate, water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo 370 mg of 4-Ethyl-7-methyl-benzo[b]thiophen-5-ol, 98%

Sources & evidence

ORD record
ord-651e502f7b584262a7f0a27158831396
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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