p-Toluenesulfonic acid monohydrate → HCID 22713244, compound

HRID 351541Notes

Reaction equation

HRID 351541 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:28])[CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:18][CH:17]=2)=O)=[CH:7][CH:6]=1)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.ClCCl>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[O:28][C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)=[CH:12][CH:13]=2)=[CH:17][CH:18]=1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 227132231-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione

Product 1

HCID 22713244HCID 22713244, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione (765 mg) and p-toluenesulfonic acid monohydrate (8 mg) in toluene (10 ml) was refluxed for 6 hours. The reaction mixture was diluted with dichloromethane, washed with water and brine, and dried over magnesium sulfate. The solvents were removed under reduced pressure and the precipitate was triturated with methanol, collected by filtration, washed with methanol and dried under reduced pressure to give methyl 4-[5-(4-n-pentyloxyphenyl)furan-2-yl]benzoate (665 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents were removed under reduced pressure
  4. customthe precipitate was triturated with methanol
  5. filtrationcollected by filtration
  6. washwashed with methanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cc661a095ebd4c1db6b9c497821ac971
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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