Hydrogen Peroxide → 1-[2-(4-Methoxybenzyloxycarbonyl)ethyl]1-cyclopentanecarboxylic acid

HRID 861696

Reaktionsgleichung

Reaktionsgleichung von HRID 861696
[C:1]([C:9]1([CH2:16][CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])[CH2:14]CCC[C:10]1=[O:15])(=O)[C:2]1C=CC=C[CH:3]=1.[OH:30]O>C(O)(C)(C)C.S(=O)(=O)(O)O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]([CH2:17][CH2:16][C:9]2([C:10]([OH:30])=[O:15])[CH2:14][CH2:3][CH2:2][CH2:1]2)=[O:19])=[CH:23][CH:24]=1

Komponenten

5

Edukt 2

HCID 784Hydrogen PeroxideHCID 190674772-Benzoyl-2-[2-(4-methoxybenzyloxycarbonyl)ethyl]cyclohexanone

Produkt 1

HCID 190674811-[2-(4-Methoxybenzyloxycarbonyl)ethyl]1-cyclopentanecarboxylic acidAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 2-benzoyl-2-[2-(4-methoxybenzyloxycarbonyl)-ethyl]cyclohexanone (see Preparation 9) (2.16 g, 5.47 mmol) in tert-butanol (4.3 ml) was added, dropwise, a 30% aqueous solution of hydrogen peroxide (0.74 ml, 6.56 mmol) and concentrated sulphuric acid (98% w/w, one drop) at room temperature. The mixture was stirred for 48 hours, partitioned between toluene (25 ml) and 5% aqueous sodium sulphite solution and the layers separated. The toluene layer was washed with dilute aqueous ammonia solution (25 ml of 0.880 ammonia in 200 ml of distilled water, 4×25 ml). The combined aqueous extracts were washed with toluene (25 ml), acidified to pH 2-3 with 5.ON aqueous hydrochloric acid solution and extracted with toluene (3×25 ml). The combined toluene extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as an oil, (0.746 g, 44.6%). RF. 0.16 silica, hexane/ethyl acetate 2:1). 1H-NMR (300 MHz, CDCl3):=1.45-1.59 (m, 2H), 1.65-1.78 (m, 4H), 1.98-2.06 (m, 2H), 2.12-2.22 (m, 2H), 2.34-2.46 (m, 2H), 3.84 (s, 3H), 5.06 (s, 2H), 6.91 (d, 2H), 7.31 (d, 2H) ppm. Analysis %: Found: C, 67.05; H, 7.18; C17H22O5 requires: C, 66.65; H, 7.24.

Aufarbeitung

  1. customat room temperature
  2. custompartitioned between toluene (25 ml) and 5% aqueous sodium sulphite solution
  3. customthe layers separated
  4. washThe toluene layer was washed with dilute aqueous ammonia solution (25 ml of 0.880 ammonia in 200 ml of distilled water, 4×25 ml)
  5. washThe combined aqueous extracts were washed with toluene (25 ml)
  6. extractionextracted with toluene (3×25 ml)
  7. dry with materialThe combined toluene extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d2573e400e6a4da4aff3937162b39442
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714628

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