Potassium Carbonate → 3,5-Dioxohexanoic acid

HRID 356584Notes

Reaction equation

HRID 356584 reaction equation
[OH:1][C:2]1[CH:3]=C2[C:9](=[CH:10][CH:11]=1)C=C(C(OCC)=O)C=C2.[OH:17]C1C=C2C(=CC=1)C=C(C(O)=O)C=C2.[I-].[C:32](=[O:35])([O-])[O-:33].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:9][C:10]([CH2:11][C:2]([CH2:3][C:32]([OH:33])=[O:35])=[O:1])=[O:17]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 855576-Hydroxy-2-naphthoic acidHCID 2769636Ethyl 6-hydroxy-2-naphthoate

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 6-hydroxyl-2-naphthate (49, 89 mg, 0.42 mmole) (6-hydroxy-2-naphthoic acid was obtained from TCI America and converted to the ester using standard esterification methods) and iodide (2, 177 mg, 0.42 mmole) in dimethylforamide (1 ml) was stirred with potassium carbonate (174 mg) for 14 hours. The reaction mixture was worked up with water (30 ml) and ethyl acetate (100 ml). The organic layer was washed with brine (30 ml), dried over sodium sulfate, filtered and concentrated. The crude product was purified on a silica gel column (hexane ethyl acetate, 4:1) to provide the triacetate of 3 (120 mg, 55%).

Workup

  1. washThe organic layer was washed with brine (30 ml)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column (hexane ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-71a6bdb1d083416fa504b16cd48b587d
Source dataset
uspto-grants-1998_11
Patent number
US05837689

Reaction notes

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