2,4-Dihydroxybenzaldehyde → 7-Hydroxyl-3-coumarin formic acid tert-butyl ester

HRID 272804Notes

Reaction equation

HRID 272804 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([C:15](C(C)(C)C)([C:19]([OH:21])=[O:20])[C:16]([OH:18])=O)(C)(C)C>C(O)(C)(C)C.N1CCCCC1>[C:3]([O:21][C:19]([C:15]1[C:16](=[O:18])[O:1][C:2]2[C:3]([CH:4]=1)=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=2)=[O:20])([CH3:6])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 72132,4-DihydroxybenzaldehydeHCID 20451979Di-tert-buty malonic acid

Product 1

HCID 586892757-Hydroxyl-3-coumarin formic acid tert-butyl esterYield 53.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6386tert-ButanolSolvent

Procedure

2,4-dihydroxylbenzaldehyde (0.27 g, 2 mmol) and di-tert-buty malonic acid (0.43 g, 2 mmol) are dissolved in tert-butanol (5 mL), and three drops of piperidine are added. The mixture is refluxed for 16 hours to obtain a suspension. After being placed for cooling, insoluble material is removed by filtrating. The mother liquor is concentrated, and the ethyl acetate is added with stirring. The supernatant is separated, concentrated, and chromatographed over silica gel column with petroleum/ethyl acetate (3:4) as eluent to obtain 0.14 g of 7-hydroxyl-3-coumarin carboxylic acid tert-butyl ester, yield: 22.5%.

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. customto obtain a suspension
  3. temperaturefor cooling
  4. custominsoluble material is removed
  5. filtrationby filtrating
  6. concentrationThe mother liquor is concentrated
  7. additionthe ethyl acetate is added
  8. customThe supernatant is separated
  9. concentrationconcentrated
  10. customchromatographed over silica gel column with petroleum/ethyl acetate (3:4) as eluent

Sources & evidence

ORD record
ord-7e18ed943e464eebae7f6f2217a8a662
Source dataset
uspto-grants-2008_11
Patent number
US07456205B2

Reaction notes

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