Hydrochloric Acid → 3-(2,4-Dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

HRID 1357059Notes

Reaction equation

HRID 1357059 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([O:22][CH3:23])=[CH:16][C:15]=1[OH:24])=[O:13].Cl.[CH2:26](OC(OCC)OCC)C>N1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:13])[C:14]2[C:19](=[CH:18][C:17]([O:22][CH3:23])=[CH:16][C:15]=2[O:24][CH3:26])[O:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 125083652-(2,4-Dimethoxy-phenyl)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone

Product 1

HCID 185054543-(2,4-Dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

A solution of 7 (3.2 g, 9.6 mmol) in triethylorthoformate (40 mL) and morpholine (10 mL) was heated to 120° C. for 4 hr. The reaction was allowed to cool to rt, poured into 2 N HCl and extracted with CH2Cl2. The CH2Cl2 was dried over MgSO4, concentrated and chromatographed on SiO2 (2:98 MeOH/CH2Cl2 to 4:96 (MeOH/CH2Cl2)) to give a the product 8 (1.5 g): Mp 202-204° C.; 1H NMR (CDCl3) δ 7.73 (s, 1H), 7.23 (d, 1H, J=9.0 Hz), 6.54-6.51 (m, 2H), 6.44 (d, 1H, J=2.3 Hz), 6.36 (d, 1H, J=2.3 Hz), 3.91 (s, 3H), 3.89 (s, 3H), 3.83 (s, 3H), 3.75 (s, 3H); MS FI 343 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe CH2Cl2 was dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed on SiO2 (2:98 MeOH/CH2Cl2 to 4:96 (MeOH/CH2Cl2))

Sources & evidence

ORD record
ord-e58f542f8df74567a3a4a32caffefd52
Source dataset
uspto-grants-2003_07
Patent number
US06589980B2

Reaction notes

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