7-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one → 7-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-one

HRID 1267767Notes

Reaction equation

HRID 1267767 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6889737-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-oneHCID 10176127Pyridinium chloride

Product 1

HCID 102440187-hydroxy-3-(4-hydroxyphenyl)-2H-chromen-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Methoxy-3-(4-methoxyphenyl)-chromen-2-one (21.8 g) was mixed with pyridine hydrochloride (80 g) and stirred for 1 hour at a temperature of 190° C. to 200° C. Water was added to the reaction mixture and the resulting precipitates were collected by filtration and dried under reduced pressure to give 7-hydroxy-3-(4-hydroxyphenyl)-chromen-2-one (19.6 g, Yield 100%). Diisopropylethylamine (35 ml)in dimethylformamide (70 ml) and methoxymethyl chloride (10.4 ml) were added to a solution of 7-hydroxy-3-(4-hydroxyphenyl)-chromen-2-one thus prepared (8.74 g) followed by stirring for 2 hours at 80° C. After cooling, water was added to the reaction mixture and the resulting precipitates were collected by filtration and dried under reduced pressure to give 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)chromen-2-one (8.67 g, Yield 74%).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0ff4cb3148b84fc3bd4bd9dd3a6ac19b
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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