HCID 66657067, compound → HCID 66657087, compound

HRID 2367649Notes

Reaction equation

HRID 2367649 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH3:23])[C:13]([O:19][C:20](=[O:22])[CH3:21])=[CH:14][CH:15]=3)[O:10][CH:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH3:23])[C:13]([O:19][C:20](=[O:22])[CH3:21])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66657067HCID 66657067, compound

Product 1

HCID 66657087HCID 66657087, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid 3-(4-hydroxy-phenyl)-8-methyl-4-oxo-4H-chromen-7-yl ester (26.32 g), 10% Pd/Al2O3 (12.93 g, 50%) and ethyl acetate (EtOAc) (1.5 L) were added to a hydrogenation round bottom flask (2 L). The flask was placed on the hydrogenator, evacuated, purged with nitrogen gas (×5) and hydrogen gas (×5). The reaction was monitored by HPLC. 10% Pd/Al2O3 (9 g, 35%) was added to the round bottom flask at 40 hours, indicated there was no product peak present, only starting material was present. HPLC at 62 hours indicated that the major peak was product peak with starting material peak being half height of product peak. 10% Pd/Al2O3 (5.69 g, 20%) was added to the round bottom flask to speed up reaction rate. Reaction was completed at 64 hours. The reaction mixture was filtered through celite to remove the Pd/Al2O3 catalyst, the celite was rinsed with EtOAc (1 L) to ensure majority of product was collected. The EtOAc was evaporated off on a rotary evaporator to give a yellow solid. The solid was re-crystallised in 95% EtOH (650 ml) and left in the freezer overnight. Off-white crystals were collected by suction filtration. 1HNMR in d-CDCl3 indicated the off-white crystals were 8 Acetic acid 3-(4-hydroxy-phenyl)-8-methyl-4-oxo-chroman-7-yl ester with >95% purity. The crystals were stored in a desiccator for 24 hours, and weighed (18.37 g, 69%).

Workup

  1. customevacuated
  2. custompurged with nitrogen gas (×5) and hydrogen gas (×5)
  3. addition10% Pd/Al2O3 (9 g, 35%) was added to the round bottom flask at 40 hours
  4. addition10% Pd/Al2O3 (5.69 g, 20%) was added to the round bottom flask
  5. customreaction rate
  6. customReaction
  7. waitwas completed at 64 hours
  8. filtrationThe reaction mixture was filtered through celite
  9. customto remove the Pd/Al2O3 catalyst
  10. washthe celite was rinsed with EtOAc (1 L)
  11. customwas collected
  12. customThe EtOAc was evaporated off on a rotary evaporator
  13. customto give a yellow solid
  14. customThe solid was re-crystallised in 95% EtOH (650 ml)
  15. waitleft in the freezer overnight
  16. filtrationOff-white crystals were collected by suction filtration
  17. waitThe crystals were stored in a desiccator for 24 hours

Sources & evidence

ORD record
ord-bf7e1c6b52fa47cc96a1b88583c455de
Source dataset
uspto-grants-2014_04
Patent number
US08697891B2

Reaction notes

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