Ethyl acetate hexane → 1(3H)-Isobenzofuranone,3-hydroxy-5-methyl-(9CI)

HRID 1071516Notes

Reaction equation

HRID 1071516 reaction equation
C(N(CC)[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[CH:12]=[O:13])C.CCCCCC.C(OCC)(=[O:25])C>Cl.O>[OH:25][CH:12]1[C:6]2[C:5](=[CH:10][CH:9]=[C:8]([CH3:11])[CH:7]=2)[C:4](=[O:14])[O:13]1

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 22393511HCID 22393511, compound

Product 1

HCID 151906771(3H)-Isobenzofuranone,3-hydroxy-5-methyl-(9CI)

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

N,N-diethyl-2-formyl-4-methyl-benzamide (7.98 g, 36.39 mmol) was taken up in 100 mL of 6N HCl and heated to reflux for 48 h. The reaction was then cooled to room temp and diluted with 50 mL of water. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane/ethyl acetate) Yield 4.66 g. 1H NMR (CDCl3, 300 MHz): δ 2.47 (s, 3H), 6.05 (bs, 1H), 7.12 (s, 1H), 7.33 (d, J=9, 1H), 7.95 (d, J=9, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 h
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-502ed9c9e58a4f85844d9fbfbd8032b6
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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