Sodium Hydroxide → 2-Acetyl-3-hydroxythiophene

HRID 1591534Notes

Reaction equation

HRID 1591534 reaction equation
[C:1]([C:4]1[S:5][C:6](C(OC)=O)=[CH:7][C:8]=1[OH:9])(=[O:3])[CH3:2].[OH-].[Na+]>[Cu].N1C2C(=CC=CC=2)C=CC=1>[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[OH:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 106080802-Thiophenecarboxylic acid, 5-acetyl-4-hydroxy-, methyl ester

Product 1

HCID 133523522-Acetyl-3-hydroxythiopheneYield 58%

Reagents, catalysts & solvents 1

HCID 67118996Copper quinolineCatalyst

Procedure

The above-obtained methyl 2-acetyl-3-hydroxythiophene-5-carboxylate was hydrolyzed with an aqueous solution of sodium hydroxide, the hydrolyzate was heated with copper-quinoline to be decarboxylated, thereby the objective 2-acetyl-3-hydroxythiophene was obtained (yield: 58%).

Sources & evidence

ORD record
ord-a347ccf5ee2649d3adda0b8311740e3e
Source dataset
uspto-grants-2007_11
Patent number
US07291449B2

Reaction notes

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