Methylparaben → Methyl 4-(t-butyloxyacetyloxy)benzoate

HRID 583690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583690
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=O.[OH:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.C([O-])([O-])=[O:22].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:6]([O:5][CH2:3][C:2]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)=[O:22])([CH3:9])([CH3:8])[CH3:7]

Komponenten

6

Edukt 3

HCID 7456MethylparabenHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 18928531Methyl 4-(t-butyloxyacetyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

t-Butyl bromoacetate (0.83 mL, 5.1 mmol), methyl 4-hydroxybenzoate (780 mg, 5.1 mmol) and Cs2CO3 (1.83 g, 5.6 mmol) were combined in 25 mL DMF. After 16 h, the reaction was diluted with ethyl acetate, washed with water, saturated NaHCO3, 10% KHSO4 and brine, dried (MgSO4) and concentrated providing 24-1 as a yellow oil. Rf 0.84 (silica, 50% EtOAC/hexane).

Aufarbeitung

  1. washwashed with water, saturated NaHCO3, 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-14cd9290c8114ddca16e3597b4b6c579
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929120

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