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

HRID 1677343Notes

Reaction equation

HRID 1677343 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 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 diethyl 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. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 30 min
  4. temperaturecooled
  5. washwashed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationConcentration in vacuo 370 mg of 4-Ethyl-7-methyl-benzo[b]thiophen-5-ol, 98%

Sources & evidence

ORD record
ord-eb2931835ea04874a5996b769a3dd1d1
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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