Hydrochloric Acid → Cresatin

HRID 1351086Notes

Reaction equation

HRID 1351086 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[CH3:14][C:15]1[CH:16]=C(O)C=[CH:19][CH:20]=1.Cl>ClCCl>[C:5]([O:4][C:1]1[CH:14]=[C:15]([CH3:16])[CH:20]=[CH:19][CH:2]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 342M-CresolHCID 1049PyridineHCID 7918Acetic Anhydride

Product 1

HCID 67406CresatinYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (519 mg) and pyridine (439 mg) were added to a solution of 3-methylphenol (500 mg) in dichloromethane (10 mL), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and water successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/8) to give the title compound (583 mg).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and water successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/8)

Sources & evidence

ORD record
ord-ed2d26abd2314683940b50383a72996b
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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