Hydrochloric Acid → 4,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

HRID 749104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749104
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[BH4-].[Na+].Cl>O1CCCC1>[OH:11][CH:1]1[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=2[C:4](=[O:5])[O:6]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 4311764Sodium borohydride

Produkt 1

HCID 109097774,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranoneAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,4,5,6-tetrahydrophthalic acid anhydride (10.0 g) in tetrahydrofuran (50.0 mL) was added sodium borohydride (600 mg) in ice bath. The mixture was stirred at room temperature for 30 minutes and refluxed for 5 hours. After cooling to room temperature, 1N hydrochloric acid (10.0 mL) was added to the reaction mixture, which was concentrated. Water was added to the residue, which was extracted with ethyl acetate. The extract was washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to give the title compound (5.40 g) having the following physical data.

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationwas concentrated
  4. additionWater was added to the residue, which
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water and brine sequentially
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-7292adb0b1aa4923b80c84e5b99ceb74
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402580B2

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