6-Methylchromone-2-carboxylic Acid → 6-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

HRID 1447795Notes

Reaction equation

HRID 1447795 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7](=O)[C:6]=2[CH:15]=1>[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=2[CH:15]=1

Participants

3

Reactant 1

HCID 6887046-Methylchromone-2-carboxylic Acid

Product 1

HCID 203830736-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

6-Methyl-4-oxo-4H-1-benzopyran-2-carboxylic acid (Niviere, et al., 1965) was hydrogenated over a palladium-on-carbon catalyst to give 3,4-dihydro-6-methyl-2H-1-benzopyran-2-carboxylic acid. This acid was converted to the acid chloride with thionyl chloride and the acid chloride was converted to 9, obtained as white plates, mp: 67°-67.5° C., by treatment with 2-propenamine, all by the procedures described in Example 1.

Sources & evidence

ORD record
ord-013d0ff31a954726840ca37dc175e88d
Source dataset
uspto-grants-1979_12
Patent number
US04178380

Reaction notes

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