Acetic Acid → HCID 21959201, compound

HRID 2055033Notes

Reaction equation

HRID 2055033 reaction equation
C([O:8][C:9]1[C:14](OC)=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1[C:18](=[O:30])[O:19][C:20]2[C:25]([C:26]=1[CH3:27])=[CH:24][CH:23]=[C:22]([O:28]C)[CH:21]=2)C1C=CC=CC=1.Cl.[C:32](O)(=[O:34])C>>[OH:8][C:9]1[CH:14]=[C:13]([O:34][CH3:32])[CH:12]=[CH:11][C:10]=1[C:17]1[C:18](=[O:30])[O:19][C:20]2[C:25]([C:26]=1[CH3:27])=[CH:24][CH:23]=[C:22]([OH:28])[CH:21]=2

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 313Hydrochloric Acid2×HCID 21959204HCID 21959204, compound

Product 1

HCID 21959201HCID 21959201, compound

Conditions

Temperature
60 °C

Procedure

A solution of 3-(2-benzyloxy-3-methoxyphenyl)-7-methoxy-4-methyl-chromen-2-one (0.98 g, 2.44 mmol), prepared as in Example 4, in glacial acetic acid (8 mL) was treated with concentrated hydrochloric acid (3.5 mL) and the mixture stirred and heated to 60° C. for about 20 hours. Reaction monitoring by mass spectrum and thin layer chromatography revealed the presence of the starting material, so additional acetic acid (4 mL) and hydrochloric acid (3 mL) were added and stirring and heating continued for another 20 hours. The reaction mixture was then evaporated to dryness in vacuum and the residue diluted with water. The precipitated crystalline pinkish, solid, crude title compound was isolated by filtration, washed with water and dried. The resulting product was triturated with ether, filtered and washed with additional ether to yield the title product as a solid.

Workup

  1. customReaction monitoring by mass spectrum and thin layer chromatography
  2. additionwere added
  3. stirringstirring
  4. temperatureheating
  5. customThe reaction mixture was then evaporated to dryness in vacuum
  6. additionthe residue diluted with water
  7. customThe precipitated crystalline pinkish, solid, crude title compound was isolated by filtration
  8. washwashed with water
  9. customdried
  10. customThe resulting product was triturated with ether
  11. filtrationfiltered
  12. washwashed with additional ether

Sources & evidence

ORD record
ord-9691c086ec0c46698b7e9967654511c6
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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