Tetrahydrofuran → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 128747

Reaktionsgleichung

Reaktionsgleichung von HRID 128747
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].C(N1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])(OCC)=O.O1CCCC1>O>[C:21]1(=[O:30])[N:2]([CH:3]2[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]2)[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]12

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 31187N-CarbethoxyphthalimideHCID 516892Sodium BicarbonateHCID 522619(1s,4s)-4-Aminocyclohexan-1-ol hydrochloride

Produkt 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-aminocyclohexanol hydrochloride (6.08 g, 0.04 mole) in water (60 ml) was brought to pH 8 with aqueous sodium bicarbonate solution. N-carbethoxy-phthalimide (8.76 g, 0.04 mole) was added followed by tetrahydrofuran (until homogenous solution was obtained). The clear solution was stirred at room temperature overnight. During this time a white solid was precipitated. The tetrahydrofuran was removed in vacuo and the remaining aqueous solution was extracted with ethyl acetate until the solution was clear. The ethyl acetate extracts were combined, washed with water, dried (MgSO4) and concentrated to give 4-phthalimido cyclohexanol as a white solid (7.1 g).

Aufarbeitung

  1. customDuring this time a white solid was precipitated
  2. customThe tetrahydrofuran was removed in vacuo
  3. extractionthe remaining aqueous solution was extracted with ethyl acetate until the solution
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8ec7e128fb84498fa001bb7b74ba420b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464864

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