Hydrochloric Acid → Ethyl 7-hydroxychromane-2-carboxylate

HRID 51070Notes

Reaction equation

HRID 51070 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH:7]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.Cl>[Pd].CCO>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 11085381Ethyl 7-hydroxychromane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a large hydrogenation vessel were added ethyl 7-hydroxychromone-2-carboxylate (=ethyl 7-hydroxy-4-oxo-4H-chromene-2-carboxylate) (675.4 g, 2.88 mol), EtOH 4 liters, conc. hydrochloric acid 40 ml. The resulting suspension was combined with 5% Pd/C 68 g, and subjected to hydrogenation condition (H2, 40 psi, rt) overnight. The reaction mixture was filtered through a pad of celite to remove the catalyst. The filtrate was concentrated to give thick oily material, which solidified upon standing. Tan solid 630.1 g (98%).

Workup

  1. customsubjected to hydrogenation condition (H2, 40 psi, rt) overnight
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated
  5. customto give thick oily material, which

Sources & evidence

ORD record
ord-4b45c41df47340bbac4c6a7fe9c76a07
Source dataset
uspto-grants-2004_03
Patent number
US06713508B2

Reaction notes

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