Dichloromethane → Methanone, (2,5-dihydroxyphenyl)(4-hydroxyphenyl)-

HRID 1816407Notes

Reaction equation

HRID 1816407 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)=[O:12].Cl.N1C=CC=CC=1.C(Cl)Cl>Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 257908(2,5-dimethoxyphenyl)(4-methoxyphenyl)methanoneHCID 10176127Pyridinium chloride

Product 1

HCID 11160567Methanone, (2,5-dihydroxyphenyl)(4-hydroxyphenyl)-

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a cooled solution (0° C.) of 4-methoxybenzoyl chloride (5.1 g, 30 mmol) and 1,4-dimethoxy benzene (4.1 g, 30 mmol) in dichloroethane (100 mL) was added aluminum chloride (4.0 g, 30 mmol) and the reaction mixture was stirred at room temperature for 1 h. The reaction was then quenched with 2N HCl and the organic layer was separated and dried over MgSO4. The organic layer was concentrated to give an oil, which was purified by column chromatography(eluent 20% EtOAc/hexanes) to give an oil (4.7 g, 58% yield). The product, (2,5-dimethoxyphenyl)(4-methoxyphenyl)methanone (4.7 g, 17.2 mmol) and pyridine hydrochloride (20 g) was heated to 200° C. After 1 hr, the reaction was cooled, diluted with 2N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, and concentrated to give an oil residue. The crude product was taken up into CH2Cl2 and a solid crystallized out which was collected by filtration (3.1 g, 78% yield); 1H NMR (DMSO-d6) 10.37 (s, 1H), 9.64 (s, 1H), 9.03 (s, 1H), 7.61 (d, 2H, J=8.6 Hz), 6.86-6.75 (m, 4H), 6.67 (d, 1H); MS m/e 229 (M−H)+.

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give an oil residue
  6. customa solid crystallized out which
  7. filtrationwas collected by filtration (3.1 g, 78% yield)

Sources & evidence

ORD record
ord-0581e479b24549bf842eae4691ecd065
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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