1-(2-hydroxyphenyl)-3-(2-methoxyphenyl)propane-1,3-dione → 2'-Methoxyflavone

HRID 398017Notes

Reaction equation

HRID 398017 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[O:11]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[O:11][C:4]2[C:3]([C:8](=[O:20])[CH:9]=1)=[CH:2][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 2377721-(2-hydroxyphenyl)-3-(2-methoxyphenyl)propane-1,3-dione

Product 1

HCID 1464922'-MethoxyflavoneYield 96.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-(2-hydroxyphenyl)-3-(2-methoxyphenyl)-propan-1,3-dione (27 g, 0.1 mol) in acetic acid (130 ml) and concentrated sulfuric acid (5 ml) were placed in a flask fitted with a reflux condenser and a stirrer. The flask was heated in a bath maintained at 100° C. for an hour. Then the reaction mixture was poured onto crushed ice (750 g). The solid was filtered off, washed with water, dried and crystallized from methanol to give 24.3 g (96.2%) of the compound (m.p.: 97-98.5° C.). In the literature (J. Org. Chem., 27, 381 (1962)), 102-103° C. is given for the product melting point.

Workup

  1. customfitted with a reflux condenser and a stirrer
  2. temperatureThe flask was heated in a bath
  3. additionThen the reaction mixture was poured
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-c4d9778c1d5b43d28a8ff6097ee50ada
Source dataset
uspto-grants-2003_08
Patent number
US06610738B2

Reaction notes

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