Ethyl 5-chloro-beta-oxo-alpha,2-bis(phenylmethoxy)benzenepropanoate → 6-Chloro-3,4-dihydroxy-2H-1-benzopyran-2-one

HRID 231130Notes

Reaction equation

HRID 231130 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24]CC2C=CC=CC=2)=[C:6]([C:8](=[O:23])[CH:9]([O:15]CC2C=CC=CC=2)[C:10]([O:12]CC)=O)[CH:7]=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:24][C:10](=[O:12])[C:9]([OH:15])=[C:8]([OH:23])[C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 13704268Ethyl 5-chloro-beta-oxo-alpha,2-bis(phenylmethoxy)benzenepropanoate

Product 1

HCID 546836946-Chloro-3,4-dihydroxy-2H-1-benzopyran-2-oneYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Catalytic hydrogenation. A solution of ethyl 5-chloro-β-oxo-α,2-bis(phenylmethoxy)benzenepropanoate (0.88 g, 0.002 mol) in 20 ml of EtOAc was hydrogenated over 0.18 g of 10% Pd/C at room temperature and 35 psi for 2 h. After filtration, the solvent was removed under reduced pressure affording a light yellow oil. The oil was treated as previously described, affording 0.293 g (69%) of 6-chloro-3,4-dihydroxy-2H-1-benzopyran-2-one as white solid.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed under reduced pressure
  3. customaffording a light yellow oil
  4. additionThe oil was treated

Sources & evidence

ORD record
ord-9e4c7d8998e34a8aaf7b8653ff4ccbec
Source dataset
uspto-grants-1989_07
Patent number
US04845121

Reaction notes

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